GB1344548A - Benzimidazole derivatives - Google Patents

Benzimidazole derivatives

Info

Publication number
GB1344548A
GB1344548A GB3866871A GB3866871A GB1344548A GB 1344548 A GB1344548 A GB 1344548A GB 3866871 A GB3866871 A GB 3866871A GB 3866871 A GB3866871 A GB 3866871A GB 1344548 A GB1344548 A GB 1344548A
Authority
GB
United Kingdom
Prior art keywords
prepared
nitro
methylamino
chloro
nitrobenzene
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
Application number
GB3866871A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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.)
Filing date
Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of GB1344548A publication Critical patent/GB1344548A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/28—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical

Abstract

1344548 Benzimidazoles AGFA-GEVAERT AG 18 Aug 1971 [20 Aug 1970] 38668/71 Heading C2C [Also in Divisions C4 and G2] The invention comprises novel benzimidazoles of Formula I when R<SP>1</SP> and R<SP>2</SP> are the same or different and represent H, C 1 -C 3 alkyl, aralkyl, aryl, halogen, CF 3 , CN, SO 2 R, SOR or SO 2 NR 2 where R = alkyl or aryl; R<SP>3</SP> and R<SP>4</SP> are the same or different and represent H or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aryl, or heterocyclic radicals; R<SP>5</SP> = H or optionally substituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or OH, SH, OR, SR or NR 2 , where R = alkyl. The compounds are prepared by (a) reacting an o-nitroaniline of formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are as defined above and Hal = halogen with a mercaptan of formula R<SP>4</SP>-SH where R<SP>4</SP> is as defined above, or with a salt thereof, (b) reducing the nitro group in known manner and (c) cyclizing in known manner to form a mercapto or thioether substituted benzimidazole. 1 - Phenylamino - 2 - nitro - 4 - chloro - 5- phenylthiobenzene and 2 - nitro - 4 - chloro - 5- phenylthio-N-methyl aniline are prepared by reacting the corresponding 4,5-dichloro compound with thiophenol in the presence of sodium carbonate. 2 - Amino - 4 - chloro - 5 - phenylthio - N - methylaniline is prepared by the hydrogenation of the corresponding 2-nitrocompound using Raney nickel. 1 - (# - Dimethylaminopropylamino) - 2- nitro-4,5-dichlorobenzene is prepared by reaction of the corresponding 1,4,5-trichloro-2-nitrobenzene with 3-amino- #-dimethylaminopropane in the presence of sodium carbonate and is reacted with 2-hydroxyethylmercaptan in the presence of sodium carbonate to obtain 1-(#- dimethylaminopropylamino)- 2 - nitro - 4 - chloro- 5-(#-hydroxyethylthio)-benzene. 1 - Chloro - 3 - methylamino - 4 - nitrobenzene is prepared by reaction of 2,4-dichloronitrobenzene with methylamine and is further reacted with thiophenol to obtain 1-phenyl-3- methylamino-4-nitrobenzene. 1 - Nitro - 2 - methylamino - 4 - carboxymethylthio-5-chlorobenzene is prepared from 4,5-dichloro - 2 - methylamino - 1 - nitrobenzene by reaction with thioglycollic acid. 1 - Nitro - 2 - methylamino 4 - dodecylthio - 5- chlorobenzene is prepared by reaction of the corresponding 4,5-dichloro compound with dodecyl mercaptan.
GB3866871A 1970-08-20 1971-08-18 Benzimidazole derivatives Expired GB1344548A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702041324 DE2041324A1 (en) 1970-08-20 1970-08-20 New benzimidazole derivatives and a process for their preparation

Publications (1)

Publication Number Publication Date
GB1344548A true GB1344548A (en) 1974-01-23

Family

ID=5780238

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3866871A Expired GB1344548A (en) 1970-08-20 1971-08-18 Benzimidazole derivatives

Country Status (4)

Country Link
BE (1) BE770911A (en)
DE (1) DE2041324A1 (en)
FR (1) FR2104619A5 (en)
GB (1) GB1344548A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2815675A1 (en) * 1977-04-12 1978-10-19 Ciba Geigy Ag ANTHELMINTICA
CN117757458A (en) * 2024-02-22 2024-03-26 广饶六合化工有限公司 Quaternary ammonium salt compound clay stabilizer

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH634306A5 (en) * 1977-04-12 1983-01-31 Ciba Geigy Ag BENZIMIDAZOLE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND ANTHELMINTIC AGENTS CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENTS.
TR20258A (en) * 1978-07-15 1980-12-08 Celamerck Gmbh & Co Kg 2-chloro-6-nitroaniline
HU184780B (en) * 1980-09-17 1984-10-29 Chinoin Gyogyszer Es Vegyeszet Process for producing thiocyanato-benzimidazoles
IL61232A (en) * 1979-10-19 1985-09-29 Chinoin Gyogyszer Es Vegyeszet Process for the preparation of 2-amino(or alkoxycarbonylamino)-5(6)-thiocyanato(or thiol)benzimidazole derivatives
HU182794B (en) * 1980-03-19 1984-03-28 Chinoin Gyogyszer Es Vegyeszet Process for producing 5-bracket-6-bracket closed-thiocyanato-benzimidazolyl-alkyl-carbamates and salts
JPS62246587A (en) * 1986-03-17 1987-10-27 ピ−ピ−ジ−　インダストリイズ，インコ−ポレイテツド Substituted benzoxazolone (or benzothiazolone) compound having herbicidal activity

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2815675A1 (en) * 1977-04-12 1978-10-19 Ciba Geigy Ag ANTHELMINTICA
CN117757458A (en) * 2024-02-22 2024-03-26 广饶六合化工有限公司 Quaternary ammonium salt compound clay stabilizer
CN117757458B (en) * 2024-02-22 2024-04-19 广饶六合化工有限公司 Quaternary ammonium salt compound clay stabilizer

Also Published As

Publication number Publication date
DE2041324A1 (en) 1972-02-24
FR2104619A5 (en) 1972-04-14
BE770911A (en) 1972-02-04

Similar Documents

Publication Publication Date Title
SU648097A3 (en) Method of obtaining derivatives
GB1138529A (en) Novel imidazole derivatives and a process for the manufacture thereof
SE421001B (en) INTERMEDIATE FOR USE FOR THE PREPARATION OF 1,2,5-THIADIAZOLIC COMPOUNDS AND PROCEDURE FOR PREPARING THIS
GB1344548A (en) Benzimidazole derivatives
GB1229141A (en)
GB1217974A (en) Ethene derivatives
GB1452448A (en) Derivatives of 2-amino-1,3-thiazine
GB1435462A (en) Photographic silver halide materials
ES386586A1 (en) N-phenyl-n-disubstituted aminoalkyl-2-amino indanes
GB1451403A (en) Silver salt containing image receiving material
GB1341863A (en) Thiazole derivatives and their use as plant growth control agents
ES395380A1 (en) N-phenylthiocarbamoylthio-hydroximate pesticides
GB1034940A (en) Benzene-sulphonyl-ureas
GB1439838A (en) Process for the preparation of diphenylamine and substituted derivatives thereof
GB1256620A (en)
GB1323227A (en) Light sensitive silver halide photographic material
GB1304098A (en)
GB1473289A (en) Process for the alpha-chlorination of alkyl chloroaromatic compounds
GB1530629A (en) 5-nitroimidazole derivatives
GB1036747A (en) Gold aryl mercaptides
ES414364A1 (en) Sulphone salts deriving from 2,5-dihydroxy benzene monosulphonic and 2,5-dihydroxy genzene disulphonic acids
GB1480429A (en) Ethers and thioethers and their use as pesticides
GB1301715A (en)
GB1345621A (en) Ether and sulphide meta-substituted phenyl ureas and their utility as herbicides
GB1448907A (en) Furanes their manufacture and use

Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees