GB343072A - Manufacture of benzimidazolone-stibinic acids - Google Patents
Manufacture of benzimidazolone-stibinic acidsInfo
- 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
Links
- ZYQXNJZUKJBRML-UHFFFAOYSA-M benzimidazol-2-one stibinic acid Chemical class [SbH2](O)=O.N=1C(N=C2C1C=CC=C2)=O ZYQXNJZUKJBRML-UHFFFAOYSA-M 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- HAVSRAMAYFTTFU-UHFFFAOYSA-N 6-amino-4-chlorobenzimidazol-2-one Chemical compound C1=C(N)C=C(Cl)C2=NC(=O)N=C21 HAVSRAMAYFTTFU-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
- 230000000397 acetylating effect Effects 0.000 abstract 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- MWZAMPYHMUSARJ-UHFFFAOYSA-M stibinic acid Chemical compound O[SbH2]=O MWZAMPYHMUSARJ-UHFFFAOYSA-M 0.000 abstract 2
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 abstract 1
- PNDJSMFFLOHKTJ-UHFFFAOYSA-N 1-n-ethyl-4-nitrobenzene-1,2-diamine Chemical compound CCNC1=CC=C([N+]([O-])=O)C=C1N PNDJSMFFLOHKTJ-UHFFFAOYSA-N 0.000 abstract 1
- MNIKERWISBANET-UHFFFAOYSA-N 1-n-methyl-4-nitrobenzene-1,2-diamine Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1N MNIKERWISBANET-UHFFFAOYSA-N 0.000 abstract 1
- CRXVBLLLPNWFBS-UHFFFAOYSA-N 4-aminobenzimidazol-2-one Chemical class NC1=CC=CC2=NC(=O)N=C12 CRXVBLLLPNWFBS-UHFFFAOYSA-N 0.000 abstract 1
- MHEBKJBEJUTXJQ-UHFFFAOYSA-N 6-amino-3-methyl-1h-benzimidazol-2-one Chemical compound C1=C(N)C=C2NC(=O)N(C)C2=C1 MHEBKJBEJUTXJQ-UHFFFAOYSA-N 0.000 abstract 1
- AULVRSFKYICAMA-UHFFFAOYSA-N N-[5-amino-2-(2-oxopropylamino)phenyl]acetamide Chemical compound NC1=CC(=C(C=C1)NCC(C)=O)NC(C)=O AULVRSFKYICAMA-UHFFFAOYSA-N 0.000 abstract 1
- FQGKHXVJDYQAAZ-UHFFFAOYSA-M [SbH2](O)=O.NC1=C(C=CC=C1)N Chemical class [SbH2](O)=O.NC1=C(C=CC=C1)N FQGKHXVJDYQAAZ-UHFFFAOYSA-M 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony 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.
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) |
-
1929
- 1929-11-07 GB GB33989/29A patent/GB343072A/en not_active Expired
-
1930
- 1930-02-19 GB GB5545/30A patent/GB343744A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB343744A (en) | 1931-02-26 |
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