GB743505A - Improvements in or relating to pyrazole derivatives - Google Patents
Improvements in or relating to pyrazole derivativesInfo
- Publication number
- GB743505A GB743505A GB1506953A GB1506953A GB743505A GB 743505 A GB743505 A GB 743505A GB 1506953 A GB1506953 A GB 1506953A GB 1506953 A GB1506953 A GB 1506953A GB 743505 A GB743505 A GB 743505A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- formamidine
- phenyl
- pyrazolinyl
- pyrazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003217 pyrazoles Chemical class 0.000 title abstract 2
- -1 1 - phenyl - pyrazolinyl Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- IJHMBLNPEYRWOL-UHFFFAOYSA-N 1-(3-methylphenyl)pyrazol-3-amine Chemical compound CC1=CC=CC(N2N=C(N)C=C2)=C1 IJHMBLNPEYRWOL-UHFFFAOYSA-N 0.000 abstract 1
- GZDIUHKAZLMQFJ-UHFFFAOYSA-N 1-(4-bromophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C(Br)C=C1 GZDIUHKAZLMQFJ-UHFFFAOYSA-N 0.000 abstract 1
- JCXFGGQGVSUHGX-UHFFFAOYSA-N 1-(4-chlorophenyl)-N-(2-phenyl-1,3-dihydropyrazol-5-yl)methanimine Chemical compound ClC1=CC=C(C=NC=2NN(CC2)C2=CC=CC=C2)C=C1 JCXFGGQGVSUHGX-UHFFFAOYSA-N 0.000 abstract 1
- SHCVEWFQFUKSDP-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrazol-3-amine Chemical compound N1=C(N)C=CN1C1=CC=C(Cl)C=C1 SHCVEWFQFUKSDP-UHFFFAOYSA-N 0.000 abstract 1
- RZXDPVYHYSEUIZ-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1CN1N=C(N)C=C1 RZXDPVYHYSEUIZ-UHFFFAOYSA-N 0.000 abstract 1
- QENUTIJJGGTTPE-UHFFFAOYSA-N 2-phenyl-3,4-dihydropyrazol-5-amine Chemical compound C1CC(N)=NN1C1=CC=CC=C1 QENUTIJJGGTTPE-UHFFFAOYSA-N 0.000 abstract 1
- RRYCYBOUQALXRP-UHFFFAOYSA-N 5-methyl-1-phenylpyrazol-3-amine Chemical compound CC1=CC(N)=NN1C1=CC=CC=C1 RRYCYBOUQALXRP-UHFFFAOYSA-N 0.000 abstract 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- DGZCNAKXRKGNTL-UHFFFAOYSA-N N,N-bis(1H-pyrazol-5-yl)methanimidamide Chemical compound N1N=C(C=C1)N(C=N)C1=NNC=C1 DGZCNAKXRKGNTL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 3-amino-1-arylpyrazoles of the formula <FORM:0743505/IV(a)/1> where Ar is an aryl radical which may be substituted, and R is hydrogen, alkyl, aryl or aralkyl. These are made from the corresponding 3-amino-1-aryl-pyrazolines by reaction with an aromatic aldehyde to give a Schiff's base or with ethyl orthoformate to give an N : N1-dipyrazolinyl-formamidine, oxidizing with a nonacid reagent (e.g. sodium or potassium permanganate) and treating the product with an aqueous acid to effect hydrolysis. The intermediate arylidene-amino-pyrazole or di-pyrazolyl-formamidine may or may not be isolated. The products may be diazotized, acylated (e.g. acetylated) or converted into sulphonamides. Examples show the production of 3-amino-1-phenylpyrazole, 3 - amino - 1 - p - chlorophenylpyrazole, 3 - amino - 1 : 5 - diphenylpyrazole, 3 - amino - 1 - p - anisyl - pyrazole, 3 - amino - 1 - p - bromophenyl - pyrazole, 3 - amino - 1 - m - tolyl pyrazole and 3 - amino - 5 - methyl - 1 - phenyl-pyrazole. Intermediates isolated are N : N1 - di - (1 - phenyl - pyrazolinyl - 3) - formamidine, N : N1 - di - (1 - p - chlorophenylpyrazolinyl - 3) - formamidine, N : N1 - di - (1 : 5-diphenyl-pyrazolinyl-3)-formamidine, N : N1-di-(1 - p - bromophenyl - pyrazolinyl - 3) - formamidine, N : N1 - di - (1 - p - anisyl - pyrazolinyl - 3) - formamidine, N : N1 - di - (1 - m - tolyl - pyrazolinyl - 3) - formamidine, N : N1 - di - (5 - methyl - 1 - phenyl - pyrazolinyl - 3) - formamidine, 3 - p - chlorobenzalamino - 1 - phenyl-pyrazoline and N : N1-di-(1-phenyl-pyrazolyl - 3) - formamidine. In general R may be hydrogen, methyl, ethyl, propyl, butyl, benzyl, phenyl or naphthyl, and Ar may be phenyl or naphthyl, optionally substituted by alkyl, alkoxy, halogen or sulphonic ester groups. According to the Provisional Specification pyrazoles of the formula <FORM:0743505/IV(a)/2> may be made by the above process, R1 and R2 being hydrogen or hydrocarbon groups such as alkyl, aryl or aralkyl.ALSO:Azo dyes are made by coupling to diazotized 3-amino-1-aryl-pyrazoles which may contain a hydrocarbon substituent in the 5-position (and/or 4-position according to the Provisional Specification).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1506953A GB743505A (en) | 1953-05-29 | 1953-05-29 | Improvements in or relating to pyrazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1506953A GB743505A (en) | 1953-05-29 | 1953-05-29 | Improvements in or relating to pyrazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB743505A true GB743505A (en) | 1956-01-18 |
Family
ID=10052488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1506953A Expired GB743505A (en) | 1953-05-29 | 1953-05-29 | Improvements in or relating to pyrazole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB743505A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3198791A (en) * | 1960-04-26 | 1965-08-03 | Hoechst Ag | New sulfanilamido-pyrazoles and process of preparing them |
| EP0119449A1 (en) * | 1983-02-11 | 1984-09-26 | The Wellcome Foundation Limited | Aminopyrazoline derivatives |
| US4810719A (en) * | 1984-05-12 | 1989-03-07 | Fisons Plc | Anti-inflammator 1,n-diarylpyrazol-3-amines |
-
1953
- 1953-05-29 GB GB1506953A patent/GB743505A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3198791A (en) * | 1960-04-26 | 1965-08-03 | Hoechst Ag | New sulfanilamido-pyrazoles and process of preparing them |
| EP0119449A1 (en) * | 1983-02-11 | 1984-09-26 | The Wellcome Foundation Limited | Aminopyrazoline derivatives |
| US4810719A (en) * | 1984-05-12 | 1989-03-07 | Fisons Plc | Anti-inflammator 1,n-diarylpyrazol-3-amines |
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