GB1350277A - Process for the manufacture of a benzimidazole derivative - Google Patents

Process for the manufacture of a benzimidazole derivative

Info

Publication number
GB1350277A
GB1350277A GB1350277DA GB1350277A GB 1350277 A GB1350277 A GB 1350277A GB 1350277D A GB1350277D A GB 1350277DA GB 1350277 A GB1350277 A GB 1350277A
Authority
GB
United Kingdom
Prior art keywords
methyl
benzoyl
benzothiadiazines
resulting
ylcarbamate
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
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of GB1350277A publication Critical patent/GB1350277A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines
    • 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
    • C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Abstract

1350277 Benzimidazole derivative IMPERIAL CHEMICAL INDUSTRIES Ltd 9 Aug 1972 [22 Sept 1971] 44203/71 Heading C2C Methyl 5(6) - benzoylbemzimidazol - 2 - ylcarbamate is prepared by reacting 2,1,4-benzothiadiazines of the formula wherein the benzoyl group is in the 6- or 7- position, n is 0 or 1, and R<SP>1</SP> is H or a carboxylic acyl radical of up to 7 carbon atoms, with acids or with triphenylphosphine, or when R<SP>1</SP> is a carboxylic acyl radical, with bases. Benzothiadiazines of the above formula are obtained by reacting 4-(or 5-)benzoyl-2-nitroaniline with methyl isocyanatoformate, reducing the resulting methyl 4 - (or 5) - benzoyl-2-nitrophenylthiocarbamoylcarbamate with an alkali metal dithionite in alkaline solution, and if desired acylating or oxidizing the resulting benzothiadiazines. Methyl 6 - benzoyl - 1H - 2,1,4 - benzothiadazin- 3-ylcarbamate is prepared by oxidizing methyl 2 - amino - 5 - benzoylphenylthiocarbamoylcarbamate, resulting from the reaction between 2- amino-4-benzoylaniline and methyl isocyanatoformate, with N-chlorosuccinimide.
GB1350277D 1971-09-22 1971-09-22 Process for the manufacture of a benzimidazole derivative Expired GB1350277A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4420371 1971-09-22

Publications (1)

Publication Number Publication Date
GB1350277A true GB1350277A (en) 1974-04-18

Family

ID=10432238

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1350277D Expired GB1350277A (en) 1971-09-22 1971-09-22 Process for the manufacture of a benzimidazole derivative

Country Status (3)

Country Link
AU (1) AU463689B2 (en)
DE (1) DE2246605A1 (en)
GB (1) GB1350277A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4060636A (en) 1976-06-10 1977-11-29 Rohm And Haas Company Acetyl- and carbalkoxythioureidobenzophenones as anthelmintic agents
US4310537A (en) 1976-06-10 1982-01-12 Rohm And Haas Company Acetyl- and carbalkoxythioureidobenzophenones
CN113956205A (en) * 2021-12-21 2022-01-21 山东国邦药业有限公司 Preparation method of mebendazole

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2541742C2 (en) * 1975-09-19 1983-04-28 Hoechst Ag, 6230 Frankfurt o-Nitro-phenyl-thionocarbamoyl-carbaminate and process for their preparation
DE2840927A1 (en) * 1978-09-20 1980-04-10 Bayer Ag 3,4-DIHYDROISOCHINOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4060636A (en) 1976-06-10 1977-11-29 Rohm And Haas Company Acetyl- and carbalkoxythioureidobenzophenones as anthelmintic agents
US4310537A (en) 1976-06-10 1982-01-12 Rohm And Haas Company Acetyl- and carbalkoxythioureidobenzophenones
CN113956205A (en) * 2021-12-21 2022-01-21 山东国邦药业有限公司 Preparation method of mebendazole

Also Published As

Publication number Publication date
AU463689B2 (en) 1975-07-09
DE2246605A1 (en) 1973-03-29
AU4601072A (en) 1974-03-07

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Legal Events

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