CH660730A5 - Verfahren zur herstellung von 3,4,5-trimethoxy-benzonitril. - Google Patents

Verfahren zur herstellung von 3,4,5-trimethoxy-benzonitril. Download PDF

Info

Publication number: CH660730A5
Authority: CH; Switzerland
Prior art keywords: trimethoxy; benzonitrile; moles; benzoic acid; acid
Prior art date: 1983-12-23

Application number

CH6072/84A

Other languages

German (de)

English (en)

Inventor

Istvan Dr Orban

Ferenc Dr Nagy

Tibor Galambos

Kalman Dr Nagy

Laszlo Boda

Zsuzsanna-Kloetzl Molnarka

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Priority date (The priority date 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 date listed.)

1983-12-23

Filing date

1984-12-20

Publication date

1987-06-15

1984-12-20 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1987-06-15 Publication of CH660730A5 publication Critical patent/CH660730A5/de

Links

OSBQUSPVORCDCU-UHFFFAOYSA-N 3,4,5-trimethoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(OC)=C1OC OSBQUSPVORCDCU-UHFFFAOYSA-N 0.000 title claims description 38
238000004519 manufacturing process Methods 0.000 title description 6
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims description 74
238000000034 method Methods 0.000 claims description 44
IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
239000004202 carbamide Substances 0.000 claims description 15
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
239000000706 filtrate Substances 0.000 claims description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
150000001983 dialkylethers Chemical class 0.000 claims description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
238000000605 extraction Methods 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
GGNMTJKRHHLJHH-UHFFFAOYSA-N Trimethylaethergallussaeure-amid Natural products COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002611 lead compounds Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
-1 propylene glycol) Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 2
QVZGKUBQTJBLKI-WDZFZDKYSA-N (nz)-n-[(3,4,5-trimethoxyphenyl)methylidene]hydroxylamine Chemical compound COC1=CC(\C=N/O)=CC(OC)=C1OC QVZGKUBQTJBLKI-WDZFZDKYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000004035 construction material Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
235000019838 diammonium phosphate Nutrition 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000005802 health problem Effects 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000563 toxic property Toxicity 0.000 description 1
229960001082 trimethoprim Drugs 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH6072/84A 1983-12-23 1984-12-20 Verfahren zur herstellung von 3,4,5-trimethoxy-benzonitril. CH660730A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU834438A HU191909B (en)	1983-12-23	1983-12-23	Process for production of 3,4,5-trimetoxi-benzonitril

Publications (1)

Publication Number	Publication Date
CH660730A5 true CH660730A5 (de)	1987-06-15

Family

ID=10967960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6072/84A CH660730A5 (de)	1983-12-23	1984-12-20	Verfahren zur herstellung von 3,4,5-trimethoxy-benzonitril.

Country Status (17)

Country	Link
JP (1)	JPS60214767A (it)
CN (1)	CN85101310A (it)
BE (1)	BE901284A (it)
CH (1)	CH660730A5 (it)
CS (1)	CS1024484A2 (it)
DE (1)	DE3446871A1 (it)
ES (1)	ES8600735A1 (it)
FI (1)	FI845107L (it)
FR (1)	FR2557106A1 (it)
GB (1)	GB2151626B (it)
HU (1)	HU191909B (it)
IT (1)	IT1178793B (it)
NL (1)	NL8403885A (it)
PL (1)	PL251144A1 (it)
RO (1)	RO92934B (it)
SE (1)	SE8406578L (it)
SU (1)	SU1452477A3 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103772236B (zh) *	2014-01-15	2016-04-13	华侨大学	一种苯甲腈衍生物的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH494210A (de) *	1968-03-27	1970-07-31	Sandoz Ag	Verfahren zur Herstellung von Nitrilen
JPS5476544A (en) *	1977-11-26	1979-06-19	Sumitomo Chem Co Ltd	Preparation of p-cyanophenol
JPS5495541A (en) *	1978-01-06	1979-07-28	Sumitomo Chem Co Ltd	Production of cyanophenol

1983
- 1983-12-23 HU HU834438A patent/HU191909B/hu not_active IP Right Cessation
1984
- 1984-12-17 BE BE1/11154A patent/BE901284A/fr not_active IP Right Cessation
- 1984-12-20 CH CH6072/84A patent/CH660730A5/de not_active IP Right Cessation
- 1984-12-21 SE SE8406578A patent/SE8406578L/xx not_active Application Discontinuation
- 1984-12-21 SU SU847773698A patent/SU1452477A3/ru active
- 1984-12-21 JP JP59268716A patent/JPS60214767A/ja active Pending
- 1984-12-21 NL NL8403885A patent/NL8403885A/nl not_active Application Discontinuation
- 1984-12-21 FI FI845107A patent/FI845107L/fi not_active Application Discontinuation
- 1984-12-21 GB GB08432498A patent/GB2151626B/en not_active Expired
- 1984-12-21 IT IT24230/84A patent/IT1178793B/it active
- 1984-12-21 DE DE19843446871 patent/DE3446871A1/de not_active Withdrawn
- 1984-12-21 RO RO116816A patent/RO92934B/ro unknown
- 1984-12-21 CS CS8410244A patent/CS1024484A2/cs unknown
- 1984-12-21 FR FR8419641A patent/FR2557106A1/fr active Pending
- 1984-12-21 PL PL25114484A patent/PL251144A1/xx unknown
- 1984-12-21 ES ES538924A patent/ES8600735A1/es not_active Expired
1985
- 1985-04-01 CN CN198585101310A patent/CN85101310A/zh active Pending

Also Published As

Publication number	Publication date
FI845107L (fi)	1985-06-24
FR2557106A1 (fr)	1985-06-28
FI845107A0 (fi)	1984-12-21
IT1178793B (it)	1987-09-16
ES538924A0 (es)	1985-11-01
CN85101310A (zh)	1987-01-24
PL251144A1 (en)	1985-10-08
DE3446871A1 (de)	1985-07-11
SU1452477A3 (ru)	1989-01-15
IT8424230A0 (it)	1984-12-21
RO92934A (ro)	1987-12-31
SE8406578D0 (sv)	1984-12-21
GB2151626A (en)	1985-07-24
GB2151626B (en)	1987-04-29
GB8432498D0 (en)	1985-02-06
CS1024484A2 (en)	1988-07-15
BE901284A (fr)	1985-06-17
RO92934B (ro)	1988-01-01
HUT36085A (en)	1985-08-28
HU191909B (en)	1987-04-28
SE8406578L (sv)	1985-06-24
ES8600735A1 (es)	1985-11-01
NL8403885A (nl)	1985-07-16
JPS60214767A (ja)	1985-10-28

Legal Events

Date	Code	Title	Description
1989-08-31	PL	Patent ceased

Publication	Publication Date	Title
DE2316377C3 (de)	1978-11-02	Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen
EP0086324A2 (de)	1983-08-24	Verfahren zur Herstellung von Ascorbinsäure
EP0002460B1 (de)	1980-06-25	Verfahren zur Herstellung von 3,4-Methylendioxymandelsäure
EP0048373A2 (de)	1982-03-31	Verfahren zur Herstellung von Pyrazol
DD239591A5 (de)	1986-10-01	Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoesaeure
CH660730A5 (de)	1987-06-15	Verfahren zur herstellung von 3,4,5-trimethoxy-benzonitril.
EP0134934B1 (de)	1987-03-04	2-Ketosulfonamide und Verfahren zu deren Herstellung
CH419169A (de)	1966-08-31	Verfahren zur Herstellung von neuen pharmakologisch wirksamen Hydroxylaminen
EP0166214B1 (de)	1989-07-26	Verfahren zur Herstellung von Succinylobernsteinsäuredialkylestern
CH633279A5 (de)	1982-11-30	Verfahren zur herstellung von 2-alkyl- bzw. 2-cycloalkyl-4-methyl-6-hydroxypyrimidinen.
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon
DE2558399A1 (de)	1976-07-01	Herstellung von 3,6-dichlorpicolinsaeure
DE2112778B2 (de)	1979-08-30	Verfahren zur Herstellung von 2-CyBn-S^Ae-IeITaChIOr- bzw. brombenzoesäurealkylestern
DE850297C (de)	1952-09-22	Verfahren zur Herstellung von Amidinsalzen
EP0115811A2 (de)	1984-08-15	2,4-Dichlor-5-thiazolcarboxaldehyd und ein Verfahren zu seiner Herstellung
CH620903A5 (it)	1980-12-31
AT259569B (de)	1968-01-25	Verfahren zur Herstellung unsymmetrisch disubstituierter Harnstoffe
AT274802B (de)	1969-10-10	Verfahren zur Herstellung von Indolderivaten
AT361473B (de)	1981-03-10	Verfahren zur herstellung von neuen thiazoli- dinderivaten und von deren saeureadditionssalzen
AT230358B (de)	1963-12-10	Verfahren zur Herstellung von neuen Benzoesäurederivaten
DE19832146B4 (de)	2007-04-05	Verfahren zur Herstellung von 3-Methylpyrazol bzw. dessen Salze
CH646167A5 (de)	1984-11-15	Verfahren zur herstellung von apovincaminsaeureestern.
CH667655A5 (de)	1988-10-31	Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen.
EP0166685A1 (de)	1986-01-02	Verfahren zur Herstellung von Alpha-Chloracetessigsäuremonomethylamid
CH655113A5 (de)	1986-03-27	Verfahren zur herstellung von n6,9-disubstituierten adeninen.