CN100572362C - A kind of diphenyl-imidazole compound and preparation method thereof - Google Patents
A kind of diphenyl-imidazole compound and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to a kind of diphenyl-imidazole compound and preparation method thereof, be used for the organic soldering flux protective membrane of printed-wiring board (PWB) treatment solution, it disclose 2-(3 ', 4 '-dimethoxy phenyl) chemical structural formula of 4-phenyl-5-Methylimidazole, and the preparation method is disclosed for generating 3 with Vanillin by methylation reaction, 4-dimethoxy benzaldehyde B, latter B and 1-phenyl 1, the reflux generation condensation reaction in glacial acetic acid of 2-propanedione C, ammonium acetate D and auxiliary agent gets compd A, suitable ratio of components mol/mol:B: C: D=1: 1: 5-9; Reaction back recovery part acetate through the ammoniacal liquor neutralization, is separated out solid again, filter crude product, after washing, purifying, be white solid again.Solvability in the water-soluble and acidic solution of the present invention is good, and compd A is precipitation-free in use, has guaranteed the quality of its utilization ratio height and printed circuit board, and raw material is easy to get, and the reaction conditions gentleness is with low cost, is fit to suitability for industrialized production.
Description
Technical field
The present invention relates to a kind of diphenyl-imidazole compound and preparation method thereof, be used for specifically the organic soldering flux protective membrane of printed circuit board treatment solution activeconstituents 2-(3 ', 4 '-dimethoxy phenyl) 4-phenyl-5-Methylimidazole and preparation method thereof.
Background technology
Diphenyl-imidazole compound has been widely used in the active ingredient in the organic soldering flux protective membrane of the printed circuit board treatment solution.In U.S. Pat 5; 560,785 (1996.10.01), US 5,498; 301 (1996.03.12), European patent EP 0; 627, in the 499A patents such as (1994.12.07), in the surface treating aqueous solution of copper and copper alloy (being organic soldering flux protective membrane treatment solution); its active constituent all is selected from the diaryl imidazole compound; particularly 2,4-diphenyl-imidazole, 2,4-phenylbenzene 5-Methylimidazole and 2-phenyl 4-benzyl imidazole.But these three biaryl compounds are water-soluble less, occur precipitation sometimes in use.Therefore influence the result of use and the utilization ratio of this activeconstituents, increased treatment step and use cost simultaneously.The manufacturing commercial city of this area has been concerned about this part thing in the world, also all is being engaged in the way of many-sided research in the hope of solving, but has the report of comparatively ideal terms of settlement few in number or fundamentally do not have a practical application up to now.
Summary of the invention
One of purpose of the present invention provides a kind of diphenyl-imidazole compound, and it is water-soluble better, and it can precipitation in use can not occur being made into acid organic soldering flux protective membrane treatment solution, guarantees the utilization ratio height of this composition and the quality of printed circuit board.
Another object of the present invention provides the preparation method of above a kind of diphenyl-imidazole compound, and its raw material is easy to get, and the reaction conditions gentleness is with low cost, is fit to suitability for industrialized production.
Technical solution of the present invention is: 2-(3 ', 4 '-dimethoxy phenyl) 4-phenyl-5-Methylimidazole chemical structural formula is:
This does not see the M.P. of the new compound A of bibliographical information, the R of thin-layer chromatography
fValue,
1H-NMR,
13C-NMR, MS and ultimate analysis EA data are as follows:
M.P.：171-172℃
TLC (silica gel F
254Plate, acetonitrile are developping agent): R
f=0.69
1H-NMR(CDCl
3)δ(ppm)：2.38(S，3H，-CH
3)
3.62-3.81(2S，2×3H，2×OCH
3)
6.77-6.79(d，1H，C
i-H)
7.22-7.54(m，7H)
13.38(S，1H，N-H)
13C-NMR(CDCl
3)δ(ppm)：149.25(S，C
g)；149.19(S，C
h)；
145.36(S，C
a)；142.06(S，C
b)；
133.18(S，C
c)；133.08(S，G
m)；
128.46(2d，2×C
o)；
126.80(2d，2×C
n)；
126.44(d，C
p)；
123.43(S，C
e)；117.56(d，C
j)；
111.22(d，C
i)；108.72(d，C
f)；
55.80(q，C
l)；55.50(q，C
k)；
12.22(q，C
d)
Ms(FAB)m/z：296(M
++2，21.0)，295(M
++1，100)，
294(M
+，51.7)，279(M
+-CH3，9.9)，154(9.0)，
136(7.1)，105(5.7)，8.3(5.8)，69(10.2)，
57(14.9)，43(15.0)
EA calculated value %:C, 73.45; H, 6.164; N, 9.516; O, 10.87
Measured value %:C, 73.16; H, 6.127; N, 9.464
Preparation method of the present invention, the first step reaction is to use Vanillin under alkaline condition, generate 3 with methyl-sulfate by methylation reaction, the 4-dimethoxy benzaldehyde, be called for short B, the second step reaction is B and the 1-phenyl 1 that abbreviates C as, the 2-propanedione, abbreviates the ratio of components of the ammonium acetate of D with mol/mol as; B: C: D=1: 1: 5-9 and auxiliary agent be reflux generation condensation reaction in glacial acetic acid, and reactant neutralizes with ammoniacal liquor after steaming most of acetate, separates out the solid, powdery thing, filter crude product, purify with organic solvent after washing, the pure product of gained are the white solid meal, M.P.171-172 ℃ again.
In the above second step condensation reaction of the present invention, optimum proportion compares mol/mol; B: C: D=1: 1: 7-8.Return time is 7-8 hour.
Add a little auxiliary SnCl in the above condensation reaction mixture
2, gained crude product color is shoaled, help purifying.
Condensation reaction gained crude product of the present invention must be again be taken up in order of priority the purifying that carries out of use with methyl alcohol and these two kinds of solvents of acetonitrile after washing.
Condensation reaction gained crude product of the present invention is to purify as solvent with acetonitrile with methyl alcohol earlier again, can obtain pure product A.
Reaction formula of the present invention is as follows:
The first step:
Second step:
The first step, the methyl reaction, the method for pressing document [Org.syn., Coll.Vol.2.P619] gets 3,4-dimethoxy benzaldehyde B white meal, M.P.43-44 ℃, productive rate 93.3%.
Second step, condensation reaction, if 3,4-dimethoxy benzaldehyde B is 1 mole, 1-phenyl 1, and the consumption of 2-propanedione C preferably also is 1 mole, because this reaction is difficult to carry out thoroughly and ammonium acetate D raw material is comparatively cheap, ratio of components on this reaction theory (mol/mol) B: C: D=1: 1: 2, actual amount D was the 5-9 mole, was preferably the 7-8 mole.
Setting-up point is more than 85 ℃, is preferably reflux temperature.Reaction times is 5-9 hour, is preferably 7-8 hour.
After reacting by heating, the reactant color becomes yellowish-brown finally dark brownly by pale yellow, and gained crude product color is very dark.In order to make the condensation reaction products color more shallow, in reaction mixture, add a small amount of tin protochloride with anti-oxidation.
When reaction finishes, check, with Merck silica gel F through TLC
254Thin layer chromatography board, ethyl acetate: sherwood oil (60-90 ℃)=1: 1 (V/V) is developping agent, observes product A spot R under the 254nm UV-light
f=0.16 obviously (shows purple fluorescence), raw material spot 3,4-dimethoxy benzaldehyde B R
f=0.56,1-phenyl 1,2-propanedione C R
f=0.62 disappears substantially.
Condensation reaction gained crude product as if being that solvent is repeatedly purified with methyl alcohol, then can be removed foreign pigment after the acetate ammonium salt is removed in washing, but checks through TLC, is developping agent with acetonitrile, removes and finds product A R
fOutside=0.69 the spot, also find R
f=0.71 small spot (being white fluorescent under the UV-light of 254nm), if be that solvent is repeatedly purified with acetonitrile, R then
f=0.71 impurity spot disappears, but difficulty is removed foreign pigment.Therefore, be that solvent is purified 2 times with methyl alcohol earlier most preferably, be that solvent is purified with acetonitrile again, just can thoroughly remove coloring matter and R
f=0.71 trace impurity, obtaining pure product is white solid, M.P.171-172 ℃.
The beneficial effect that the present invention obtains is this active compound component, and water-soluble better, in use solubleness is good to be made into acid organic soldering flux protective membrane treatment solution; precipitation-free, and raw material is easy to get the reaction conditions gentleness; with low cost, be fit to suitability for industrialized production.
Embodiment
Reagent, thin layer chromatography board:
3,4-dimethoxy benzaldehyde: preparation voluntarily.White powder, M.P.43-44 ℃, TLC[ethyl acetate: sherwood oil (60-90 ℃)=1: 1 (V/V)] R
f=0.56
1-phenyl-1,2-propanedione: for Guangdong brilliance laboratory provides.
102-104℃/1.60kpa
1H-NMR(CDCl
3)δ(ppm)：2.512(S，3H，-CH
3)
7.35-7.76(m，3H，2b，c)
7.99-8.01(m，2H，2a)
TLC Merck silica gel F
254Thin layer chromatography board.
Instrument: the INOVA 500NB of U.S. Vanian company NMR spectrometer with superconducting magnet
Day island proper Tianjin 8201 infrared spectrometers
VG ZAB-HS organic mass spectrometer
The Germany Elementar Vario EL of company elemental analyser
Embodiment one
2-of the present invention (3 ', 4 '-dimethoxy phenyl) 4-phenyl 5-Methylimidazole chemical structural formula is:
Compd A
1H-NMR,
13C-NMR, MS and ultimate analysis EA data are as follows:
1H-NMR(CDCl
3)δ(ppm)：2.38(S，3H，-CH
3)
3.62-3.81(2S，2×3H，2×OCH
3)
6.77-6.79(d，1H，C
i-H)
7.22-7.54(m，7H)
13.38(S，1H，N-H)
13C-NMR(CDCl
3)δ(ppm)：149.25(S，C
g)；149.19(S，C
h)；
145.36(S，C
a)；142.06(S，C
b)；
133.18(S，C
c)；133.08(S，C
m)；
128.46(2d，2×C
o)；
126.80(2d，2×C
n)；
126.44(d，C
p)；
123.43(S，C
e)；117.56(d，C
j)；
111.22(d，C
i)；108.72(d，C
f)；
55.80(q，C
l)；55.50(q，C
k)；
12.22(q，C
d)
Ms(FAB)m/z：296(M
++2，21.0)，295(M
++1，100)，
294(M
+，51.7)，279(M
+-CH3，9.9)，
154(9.0)，136(7.1)，105(5.7)，8.3(5.8)，
69(10.2)，57(14.9)，43(15.0)
EA calculated value (%): C, 73.45; H, 6.164; N, 9.516; O, 10.87
Measured value (%): C, 73.16; H, 6.127; N, 9.464.
2-of the present invention (3 ', 4 '-dimethoxy phenyl) preparation method of 4-phenyl 5-Methylimidazole is as follows:
The first step, methylation reaction.
Reference literature [Org.syn., Coll.Vol.2.P619]
[1]Method.Add 150mL distilled water with 30g (0.75mol) NaOH and be made into NaOH solution (stand-by).
In 36.2g (0.24mol) Vanillin, under agitation add 90mL distilled water, be heated to 100 ℃ when miscible, after adding the sodium hydroxide solution 72mL of above-mentioned preparation, slowly splash into being about to 37.8g (0.3mol) methyl-sulfate, keeping the little boiling of reaction solution bubbles, drip off and continue heating 45 minutes, this moment, pH value was about 7.Repeat four times then and add methyl-sulfate NaOH liquid, splash into 7.8g (0.062mol) methyl-sulfate and the above-mentioned NaOH liquid 12mL for preparing at every turn, reacted 20 minutes at every turn.Add 30mL NaOH liquid at last again, reacting by heating 20 minutes.Reaction solution through TLC check (developping agent is an ethyl acetate: sherwood oil (60 ℃-90 ℃)=1: 1V/V), the spot R of raw material Vanillin
f0.53 disappear, have only product B spot R
f0.56, reduce to room temperature rapidly, reaction solution merges with 4 * 100mL ether extraction, tell lower layer of water after, ether layer anhydrous Na
2SO
4Dry, after the filtration, ether is removed in distillation, gets light yellow oil, puts the refrigerator cooling curing, dry 3, the white meal 37.2g of 4-dimethoxy formaldehyde B, M.P.43-44 ℃, productive rate 93.3% is (because of adopting the method that adds methyl-sulfate and alkali mixed solution in five batches, make reaction more complete, so the productivity ratio document
[1]Value 82-87% slightly improves).Its tlc R
f, IR,
1H-NMR and MS data are as follows:
TLC[ethyl acetate: sherwood oil (60-90 ℃)=1: 1 (V/V)]: R
f=0.56
IR
max KBr(cm
-1)：3438，3090，2960，2942，2840，1687，1683，1466，1269，1178，1126，733。
1H-NMR(CDCl
3)δ(ppm)：9.86(S，1H，-CHO)
7.48(d，1H，C
6-H)
7.42(S，1H，C
2-H)
6.70(d，1H，C
5-H)
3.94-3.97(2S，2×3H，2-OCH
3)
MS(FAB)m/z：166(M
+，100％)，165(M
+-1，49％)，151(M
+-CH
3，18％)，
95(M
+-1-CHO-CH
3-C
2H
2，34％)，77(C
6H
5，19.5％)，
51(C
6H
5-C
2H
2，14％)
Second step, condensation reaction.With 3,4-dimethoxy benzaldehyde B 29.9g (0.18mol), 1-phenyl 1,2-propanedione C 26.7g (0.18mol), ammonium acetate D 69.4g (0.9mol), 0.5g SnCl
2 [1]In the 240mL glacial acetic acid reflux 7-8 hour
[2]After decompression steams 200mL acetate
[3], be cooled to room temperature, under cooling, add weak ammonia and be neutralized to PH=7.5-8.0
[4], filter the solid substance separate out, after the washing, drain, dry brown crude product 60.6g.
The crude product acetonitrile is a solvent recrystallization, and the 60.6g crude product adds acetonitrile 133.3mL, i.e. crude product (g): acetonitrile (mL)=1: 2.2 (g/mL); Heating in water bath refluxed 30 minutes, and filtered while hot is put under the refrigerator (2-4 ℃) cooling and separated out solid, suction filtration, dry 45.2g.Acetonitrile in above method and the same ratio of adding carries out purification process again.The product 34.4g that is still had color.
Product to be purified for the third time adds methyl alcohol 127.3mL, i.e. crude product (g): methyl alcohol (mL)=1: 3.7 (g/mL) by band color product 34.4g.Heating in water bath refluxed 30 minutes, filtered while hot, put refrigerator 2-4 ℃ down cooling separate out solid, suction filtration, dry 28.8g white powdery solid.But, find to remove product spot R through TLC (acetonitrile is a developping agent)
fOutside=0.69, the spot R of impurity also appears
f=0.71
[5], therefore also need use the acetonitrile recrystallization more once, recrystallization is identical for the first time with crude product with the ratio that adds acetonitrile for method therefor, obtains pure white solid at last, and M.P.171-172 ℃, output 23.6g, productive rate 44.5%.
Annotate:
[1] after reacting by heating, the reactant color is by pale yellow-yellowish-brown-dark brown variation, so preferably add 0.5gSnCl
2Anti-oxidation variable color or logical N
2Protection.
[2] check through TLC,, use ethyl acetate: sherwood oil (60-90 ℃)=1: 1 (v/v) refluxing 5 hours
Be developping agent, still have raw material 3,4-dimethoxy benzaldehyde B R
f=0.56 and 1-phenyl 1,2-propanedione C R
f=0.62 spot, backflow 7-8 hour, two raw material B, C spot disappeared only apparent product A R
f=0.16 spot.
[3] reclaim under reduced pressure acetate, favourable acetate is recycled, and reduces the ammoniacal liquor of neutralization usefulness, reduces cost, and reduces the three wastes again and handles.
[4] owing to use in the ammoniacal liquor and strong heat release, keep below the room temperature, stirring also slowly neutralizes, and not so can separate out the black oily matter of part, causes the aftertreatment difficulty and the productive rate reduction.
[5] product CH
3OH purifies, and checks that through TLC acetonitrile is a developping agent, and the product spot shows purple fluorescence, impurity spot R under the 254nm UV-light
f=0.71 whitening look fluorescence.
Product
1H-NMR,
13C-NMR, mass spectrum MS and ultimate analysis EA data are as follows:
1H-NMR(CDCl
3)δ(ppm)：2.38(S，3H，-CH
3)
3.62-3.81(2S，2×3H，2×OCH
3)
6.77-6.79(d，1H，C
f-H)
7.22-7.54(m，7H)
13.38(S，1H，N-H)
13C-NMR(CNCl3)δ(ppm)：149.5(S，C
g)；149.19(S，C
h)；
145.36(S，C
a)；142.06(S，C
b)；
133.18(S，C
c)；133.08(S，C
m)；
128.46(2d，2C
o)；126.80(2d，2C
n)；
126.44(d，C
p)；123.43(S，C
e)；
117.56(d，C
j)；111.22(d，C
i)；
108.72(d，C
f)；55.80(q，C
l)；
55.50(q，C
k)；12.22(q，C
d)。
MS(FAB)m/z(％)：296(M
++2，21.0)，295(M
++1，100)，
294(M
+，51.7)，279(M
+-CH
3，9.9)，
154(9.0)，136(7.1)，105(5.7)，83(5.8)，
69(10.2)，57(14.9)，43(15.0)
EA calculated value (%) C, 73.45; H, 6.164; N, 9.516; O, 10.87.
Measured value (%) C, 73.16; H, 6.127; N, 9.464.
By above spectrogram and ultimate analysis data, the affirmation product be 2-(3 ', 4 '-dimethoxy phenyl) structure of 4-phenyl 5-Methylimidazole.
The present invention has also measured associated sample in the time of 25.5 ℃, and the solubleness in 5% acetic acid solution, result shows, high temperature resistant organic soldering flux protective membrane commonly used 2, the solubleness of 4-diphenyl-imidazole is 0.114, and this product A is 0.494.
Annotate: high temperature resistant organic soldering flux protective membrane often uses the 5%-10% acetic acid solution
Embodiment two
Condensation reaction, charging capacity and operation are identical with embodiment one.
The method of crude product recrystallization is also identical with embodiment one with the ratio that adds solvent methanol or acetonitrile.
Crude product methyl alcohol is that solvent recrystallization purifies twice, purifies once with acetonitrile again, gets white meal, checks (acetonitrile is a developping agent) through TLC, has only the spot R of product A
f=0.69 (apparent purple fluorescence under the ultra-violet lamp).
M.P.171-172 ℃ of products therefrom A, output 26.7g, productive rate 50.4%.
1H-NMR,
13C-NMR, MS are consistent with embodiment one with the EA measurement result, and following examples three, four, five and six M.P., spectrometry and EA data are also basic identical.
Embodiment three
Operate equally with embodiment one.
But ammonium acetate D charging capacity changes 97.12g (1.26mol) into by 69.4g (0.9mol).Be dimethoxy benzaldehyde B: 1-phenyl 1,2-propanedione C: ammonium acetate D (mol/mol)=1: 1: 7.
The crude product method of purification is with embodiment two.Products therefrom A output 30.09g, productive rate 56.8%.
Embodiment four
Operate equally with embodiment one.
Ammonium acetate D charging capacity changes 110.0g (1.44mol) into.Be dimethoxy benzaldehyde B: 1-phenyl 1,2-propanedione C: ammonium acetate D (mol/mol)=1: 1: 8.
Crude product is as follows with secondary methyl alcohol purifying and the last acetonitrile re-crystallization step of using:
1. gained crude product 60.6g (brown, part contain crystal water) is added 225mL methyl alcohol, heating in water bath refluxed 30 minutes, and filtered while hot is put a refrigerator 2-4 ℃ cooling and separated out solid, drains, dry 46.6g.
2. with above-mentioned 46.6g product, add 172mL CH
3OH repeats as step 1, gets 38.3g band yellowish white powder solid.
3. for the third time,, add the 85mL acetonitrile with above-mentioned 2 gained 38.3g products, heating in water bath, stirring and refluxing 30 minutes, filtered while hot, put refrigerator 2-4 ℃ cooling, separate out solids, suction filtration, dry 2-(3 ', the 4 ' dimethoxy phenyl) 4-phenyl-pure product of 5-Methylimidazole, be white powdery solid, M.P.171-172 ℃, output 30.3g, productive rate 57.2%.
Embodiment five
Operate equally with embodiment four.
Ammonium acetate D charging capacity changes 123.75 (1.62mol) into.Promptly ratio of components B: C: D (mol/mol)=1: 1: 9, product A 30.36g, productive rate 57.3%.
Compare with embodiment four, productive rate does not obviously increase.
Embodiment six
Operation is identical with embodiment four with recrystallization method.
All charging capacitys are compared with embodiment four, increase four times.Promptly 3,4-dimethoxy benzaldehyde 119.7g (0.72mol), 1-phenyl 1,2-acetone 106.7g (0.72mol), ammonium acetate 444.0g (5.76mol).SnCl
2Also corresponding increase with glacial acetic acid.Reflux 8 hours.
Products therefrom A output 123.1g, productive rate 58.1%.
Now embodiment one～six condensation reaction ratio of components, recrystallization solvent and productive rate are listed in table one
Table one, embodiment one～six condensation reaction ratio of components, recrystallization solvent and productive rate
| Ratio of components | Embodiment one | Two | Three | Four | Five | Six |
| B∶C∶D (mol/mol) | 1∶1∶5 | 1∶1∶5 | 1∶1∶7 | 1∶1∶8 | 1∶1∶9 | 1: 1: 8 quadruplication amount |
| Return time | 7-8 hour | 7-8 hour | 7-8 hour | 7-8 hour | 7-8 hour | 8 hours |
| Recrystallization solvent and number of times | Acetonitrile (2 times) methyl alcohol (1 time) acetonitrile (1 time) | Methyl alcohol (2 times) acetonitrile (1 time) | Methyl alcohol (2 times) acetonitrile (1 time) | Methyl alcohol (2 times) acetonitrile (1 time) | Methyl alcohol (2 times) acetonitrile (1 time) | Methyl alcohol (2 times) acetonitrile (1 time) |
| Productive rate % | 44.5 | 50.4 | 56.8 | 57.2 | 57.3 | 58.1 |
Claims (8)
1, a kind of diphenyl-imidazole compound, it is characterized in that 2-(3 ', 4 '-dimethoxy phenyl) 4-phenyl-5-Methylimidazole, chemical structural formula is:
2, according to right 1 described a kind of diphenyl-imidazole compound, it is characterized in that, 2-(3 ', 4 '-dimethoxy phenyl) 4-phenyl-5-Methylimidazole, its M.P., tlc R
f,
1H-NMR,
13C-NMR spectrum, MS and ultimate analysis EA data are as follows:
M.P.：171-172℃
TLC silica gel F
254Plate, acetonitrile are developping agent: R
f=0.69
1H-NMR(CDCl
3)δ(ppm)：2.38(S，3H，-CH
3)
3.62-3.81(2S，2×3H，2×OCH
3)
6.77-6.79(d，1H，C
i-H)
7.22-7.54(m，7H)
13.38(S，1H，N-H)
13C-NMR(CDCl
3)δ(ppm)：149.25(S，C
g)；149.19(S，C
h)；
145.36(S，C
a)；142.06(S，C
b)；
133.18(S，C
c)；133.08(S，C
m)；
128.46(2d，2×C
o)；
126.80(2d，2×C
n)；
Ms(FAB)m/z：296(M
++2，21.0)，295(M
++1，100)，
294(M
+，51.7)，279(M
+-CH3，9.9)，
154(9.0)，136(7.1)，105(5.7)，8.3(5.8)，
69(10.2)，57(14.9)，43(15.0)
EA calculated value (%): C, 73.45; H, 6.164; N, 9.516; O, 10.87
Measured value (%): C, 73.16; H, 6.127; N, 9.464.
3,2-(3 ', 4 '-dimethoxy phenyl) preparation method of 4-phenyl-5-Methylimidazole, it is characterized in that under alkaline condition, methylating and generate 3 with methyl-sulfate with Vanillin, the 4-dimethoxy benzaldehyde, abbreviate B as, latter B and the 1-phenyl 1 that abbreviates C as, the 2-propanedione, abbreviate the ratio of components of the ammonium acetate of D with mol/mol as: B: C: D=1: 1: 5-9 and auxiliary agent be reflux generation condensation reaction in glacial acetic acid, behind the recovery part acetate,, separate out solid through the ammoniacal liquor neutralization, filter crude product, again through washing, through purify 2-(3 ', the 4 ' dimethoxy phenyl) 4-phenyl-pure product of 5-Methylimidazole, be white solid.
4, preparation method according to claim 3 is characterized in that the second step condensation reaction, suitable ratio of components mol/mol:B: C: D=1: 1: 7-8.
5, preparation method according to claim 3 is characterized in that the second step condensation reaction, and return time is 7-8 hour.
6, preparation method according to claim 3 is characterized in that adding in the condensation reaction mixture a little auxiliary SnCl
2, gained crude product color is shoaled, help purifying.
7, preparation method according to claim 3, it is characterized in that condensation reaction gained crude product through the washing after, must be taken up in order of priority with methyl alcohol and these two kinds of solvents of acetonitrile again and purify.
8, preparation method according to claim 3 is characterized in that condensation reaction gained crude product, is earlier to carry out recrystallization with acetonitrile as solvent again with methyl alcohol to purify, obtain 2-(3 ', 4 '-dimethoxy phenyl) the 4-phenyl-pure product of 5-Methylimidazole.
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|---|---|---|---|
| CNB2006101229850A CN100572362C (en) | 2006-10-24 | 2006-10-24 | A kind of diphenyl-imidazole compound and preparation method thereof |
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| CN101928248B (en) * | 2010-08-04 | 2012-07-25 | 和夏化学(太仓)有限公司 | Method for preparing 2-phenylimidazole compounds |
| CN102775351B (en) * | 2011-05-12 | 2015-09-30 | 比亚迪股份有限公司 | A kind of diimidazole compounds and preparation method thereof soldering flux treatment solution organic with one |
| CN105755485A (en) * | 2016-05-19 | 2016-07-13 | 四川理工学院 | Novel water soluble metal pickling corrosion inhibitor and application thereof |
| US11090289B2 (en) | 2017-01-24 | 2021-08-17 | University Of Virginia Patent Foundation | Compositions and methods for blocking sodium channels |
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| US5498301A (en) * | 1993-05-10 | 1996-03-12 | Shikoku Chemicals Corporation | Agent for treating surfaces of copper and copper alloys |
| CN1761773A (en) * | 2003-03-19 | 2006-04-19 | 四国化成工业株式会社 | Novel imidazole compound and usage thereof |
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| US5498301A (en) * | 1993-05-10 | 1996-03-12 | Shikoku Chemicals Corporation | Agent for treating surfaces of copper and copper alloys |
| CN1761773A (en) * | 2003-03-19 | 2006-04-19 | 四国化成工业株式会社 | Novel imidazole compound and usage thereof |
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Address after: Chen Dong Cun Industrial Zone Six fertile town Baiyun District of Guangzhou City, Guangdong province Guangzhou city 510545 Co-patentee after: GUANGDONG GUANGHUA SCI-TECH Co.,Ltd. Patentee after: GUANGDONG TONESET SCIENCE & TECHNOLOGY Co.,Ltd. Address before: Chen Dong Cun Industrial Zone Six fertile town Baiyun District of Guangzhou City, Guangdong province Guangzhou city 510545 Co-patentee before: Guangdong Guanghua Chemical Factory Co.,Ltd. Patentee before: GUANGDONG TONESET SCIENCE & TECHNOLOGY Co.,Ltd. |
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