GB343072A - Manufacture of benzimidazolone-stibinic acids - Google Patents

Manufacture of benzimidazolone-stibinic acids

Info

Publication number
GB343072A
GB343072A GB33989/29A GB3398929A GB343072A GB 343072 A GB343072 A GB 343072A GB 33989/29 A GB33989/29 A GB 33989/29A GB 3398929 A GB3398929 A GB 3398929A GB 343072 A GB343072 A GB 343072A
Authority
GB
United Kingdom
Prior art keywords
dihydride
oxobenzimidazole
amino
stibinic
acid
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
GB33989/29A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB343072A publication Critical patent/GB343072A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/90Antimony compounds

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)

Abstract

5-Amino-7-chloro - 2 - oxobenzimidazole - 2 : 3-dihydride is prepared by the catalytic reduction of the corresponding 5-nitro compound.ALSO:Benzimidazolone-stibinic acids are prepared either by treatment of o-diaminobenzene-stibinic acids with phosgene, or by interaction of diazotized aminobenzimidazolones with antimonious acid. The products, preferably in the form of their soluble salts with alkalies, ammonia or organic bases, are useful therapeutically. According to the examples, (1) 1-methyl-2-oxobenzimidazole-2 : 3-dihydride-5-stibinic acid is produced by introducing phosgene into a caustic soda solution of 3-amino-4-methyl-aminobenzene-1-stibinic acid; in a similar manner 3 : 4-diaminobenzene-1-stibinic acid yields 2-oxo-benzimidazole-2 : 3-dihydride-5-stibinic acid, and 3 : 4-diamino-5-chlorobenzene-1-stibinic acid gives 2 - oxobenzimidazole-2 : 3-dihydride-7-chloro-5-stibinic acid; (2) 1-methyl-2-oxobenzimidazole-2 : 3-dihydride-5-stibinic acid is prepared by diazotizing 1-methyl-5-amino - 2 - oxobenzimidazole - 2 : 3-dihydride and adding an antimonite solution obtained by dissolving antimony trioxide in caustic soda in the presence of glycerine; the diazo solution may also be caused to react with an acid solution of antimony trichloride and the resulting double compound decomposed with caustic soda; in the same way 1-ethyl-2-oxobenzimidazole-2 : 3-dihydride-5-stibinic acid is obtained from 1-ethyl-5-amino-2-oxobenzimidazole-2 : 3-dihydride, 2-oxobenzimidazole-2 : 3-dihydride-5-stibinic acid from 5-amino-2-oxobenzimidazole-2 : 3 dihydride, and 2 - oxobenzimidazole - 2 : 3 -dihydride-7-chloro-5-stibinic acid from 5-amino-7-chloro-2-oxobenzimidazole-2 : 3-dihydride. 3-Amino-4-methylaminobenzene-1-stibinic acid is prepared by treating 2 : 4-dinitro-1-chlorobenzene with methylamine, partially reducing with alkali sulphide to 4-nitro-2-amino-1-methylaminobenzene, acetylating, reducing to 4-amino-2-acetylamino-1-acetylmethylaminobenzene, converting into the stibinic acid and finally saponifying. 3 : 4-Diaminobenzene-1-stibinic acid is made by acetylating 3 : 4-diamino-1-nitrobenzene, reducing, converting into the 3 : 4-diacetyldiaminobenzene-1-stibinic acid, and saponifying. 3 : 4-Diamino-5-chlorbenzene-1-stibinic acid is obtained by reducing 6-chloro-2 : 4-dinitraniline with alkali sulphide to 6-chloro-4-nitro-1 : 2-diaminobenzene, which is acetylated, reduced, the amino group replaced by the stibinic acid residue and the product saponified. 1-Ethyl-5-amino-2-oxobenzimidazole-2 : 3-dihydride is produced by partial reduction of 1-ethylamino-2 : 4-dinitrobenzene, treatment of the resulting 1-ethylamino-2-amino-4-nitrobenzene with phosgene, followed by reduction of the nitro group. 5-Amino-2-oxobenzimidazole-2 : 3-dihydride results when 3 : 4-diamino-1-nitrobenzene is treated with phosgene and the product reduced. 5 - Amino - 7 - chloro - 2 - oxobenzimidazole - 2 : 3 - dihydride is prepared by causing phosgene to react with 6-chloro-4-nitro-1 : 2-diaminobenzene and then catalytically reducing the nitro product.
GB33989/29A 1928-11-07 1929-11-07 Manufacture of benzimidazolone-stibinic acids Expired GB343072A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE343072X 1928-11-07

Publications (1)

Publication Number Publication Date
GB343072A true GB343072A (en) 1931-02-09

Family

ID=6243544

Family Applications (2)

Application Number Title Priority Date Filing Date
GB33989/29A Expired GB343072A (en) 1928-11-07 1929-11-07 Manufacture of benzimidazolone-stibinic acids
GB5545/30A Expired GB343744A (en) 1928-11-07 1930-02-19 Manufacture of benzimidazolone-stibinic acids

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB5545/30A Expired GB343744A (en) 1928-11-07 1930-02-19 Manufacture of benzimidazolone-stibinic acids

Country Status (1)

Country Link
GB (2) GB343072A (en)

Also Published As

Publication number Publication date
GB343744A (en) 1931-02-26

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