GB659250A - Improvements in or relating to substituted benzene stibonic acids and process for the manufacture thereof - Google Patents
Improvements in or relating to substituted benzene stibonic acids and process for the manufacture thereofInfo
- Publication number
- GB659250A GB659250A GB17826/49A GB1782649A GB659250A GB 659250 A GB659250 A GB 659250A GB 17826/49 A GB17826/49 A GB 17826/49A GB 1782649 A GB1782649 A GB 1782649A GB 659250 A GB659250 A GB 659250A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxymethylmercapto
- aniline
- benzene
- carboxyalkylmercapto
- stibonic
- 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
- -1 benzene stibonic acids Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001721 carbon Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- WXJFXEYOZNYMMJ-UHFFFAOYSA-L stibonic acid Chemical compound O[SbH](O)=O WXJFXEYOZNYMMJ-UHFFFAOYSA-L 0.000 abstract 2
- AVXQREFAMKAFPA-UHFFFAOYSA-N 2-(2-amino-5-chlorophenyl)sulfanylacetic acid Chemical compound NC1=CC=C(Cl)C=C1SCC(O)=O AVXQREFAMKAFPA-UHFFFAOYSA-N 0.000 abstract 1
- YMXXVMANBGJXOY-UHFFFAOYSA-N 2-(2-amino-5-methoxyphenyl)sulfanylacetic acid Chemical compound COC1=CC=C(N)C(SCC(O)=O)=C1 YMXXVMANBGJXOY-UHFFFAOYSA-N 0.000 abstract 1
- TYRZAGMAVZESQX-UHFFFAOYSA-N 2-amino-5-chlorobenzenethiol Chemical compound NC1=CC=C(Cl)C=C1S TYRZAGMAVZESQX-UHFFFAOYSA-N 0.000 abstract 1
- QHALDOSHHZPRRB-UHFFFAOYSA-N 2-amino-5-methoxybenzenethiol Chemical compound COC1=CC=C(N)C(S)=C1 QHALDOSHHZPRRB-UHFFFAOYSA-N 0.000 abstract 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- VJVWEEPBMVCKCV-UHFFFAOYSA-N 3-(carboxymethylsulfanyl)benzoic acid Chemical compound OC(=O)CSC1=CC=CC(C(O)=O)=C1 VJVWEEPBMVCKCV-UHFFFAOYSA-N 0.000 abstract 1
- BBKWPBLTXKLLPT-UHFFFAOYSA-N 3-anilinosulfanylpropanoic acid Chemical compound C(=O)(O)CCSNC1=CC=CC=C1 BBKWPBLTXKLLPT-UHFFFAOYSA-N 0.000 abstract 1
- FPXGZTGLDMHYFS-UHFFFAOYSA-N 4-amino-3-(carboxymethylsulfanyl)benzoic acid Chemical compound C(=O)(O)CSC1=C(N)C=CC(=C1)C(=O)O FPXGZTGLDMHYFS-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000001555 benzenes Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 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
- C07F9/92—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Carboxyalkylmercapto - benzene - stibonic acids are obtained by diazotizing a carboxyalkylmercapto-aniline which is characterized in that the benzene ring is further substituted, or the carboxyalkylmercapto radical is in other than the 2-position, or the alkylene group in the carboxyalkylmercapto radical contains more than one carbon atom, reacting the diazo compound with an antimonite in the presence of copper and acidifying the reaction product. The substituted benzene ring may contain alkyl, alkoxy, halogen, carboxy, or acylamino radicals. The resulting stibonic acid may be converted into a carboxylate salt, e.g. a metal salt or a salt derived from a nitrogen-containing base. The carboxyalkylmercapto aniline may contain the carboxyalkylmercapto group in the 3- or 4-position. A carboxyethylmercapto aniline may be used for the process. In the examples, the following stibonic acids are prepared: 2-carboxyethylmercapto- and 2-(a -carboxyethylmercapto)-, 2 - carboxymethyl - mercapto - 4 - acetamino -, 2 - carboxymethylmercapto - 4 - methoxy -, 2 - carboxymethylmercapto - 4 - methyl -, 2 - carboxymethylmercapto - 4 - chloro -, 3 - and 4 - carboxymethylmercapto-, and 4-carboxy-2-carboxymethylmercapto - benzene - stilbonic acids. 4 - Carboxymethylmercapto - 2,3 - dimethyl-and 4 - carboxymethyl - 2 - methyl - benzene stibonic acids are also mentioned. 2 - Carboxymethylmercapto - 4 - chloro - aniline is prepared by condensing monochloroacetic acid and 2-mercapto-4-chloro-aniline in the presence of aqueous sodium hydroxide. 2 - Carboxymethylmercapto - 4 - methoxy - aniline is prepared by condensing 2-mercapto-4-methoxy-aniline and monochloro-acetic acid in the presence of aqueous sodium hydroxide. 2 - (b - Carboxyethylmercapto) - and 2 - (a - carboxyethylmercapto)-aniline are prepared by condensing the zinc mercaptide of 2-aminobenzenethiol and b -bromopropionic acid and a -bromopropionic acid respectively in the presence of aqueous sodium hydroxide. 4 - Methyl - and 4 - carboxy - 2 - carboxymethylmercapto-aniline are prepared by a similar method.ALSO:IV(b) Internal remedies comprise aqueous solutions of water soluble salts of car boxyalkylmercapto-benzene-stibonic acids in which the benzene ring is further sub stituted, e.g. with alkoxy, alkyl, halogen, carboxy or acylamino radicals, or the car boxyalkylmercapto radical is in position other than the 2-position of the benzene ring, or the alkyl radical in the carboxy alkylmercapto radical contains more than one carbon atom. An internal remedy also comprises a dilute solution of 3-car boxymethylmercapto-benzene-stibonic acid in diethanolamine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US255570XA | 1946-06-14 | 1946-06-14 | |
| US659250XA | 1948-07-13 | 1948-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB659250A true GB659250A (en) | 1951-10-17 |
Family
ID=26699905
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11883/47A Expired GB623488A (en) | 1946-06-14 | 1947-05-02 | A process for the manufacture of 2-carboxymethylmercapto-benzene stibonic acid |
| GB17826/49A Expired GB659250A (en) | 1946-06-14 | 1949-07-06 | Improvements in or relating to substituted benzene stibonic acids and process for the manufacture thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11883/47A Expired GB623488A (en) | 1946-06-14 | 1947-05-02 | A process for the manufacture of 2-carboxymethylmercapto-benzene stibonic acid |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH255570A (en) |
| DE (1) | DE890960C (en) |
| FR (1) | FR946090A (en) |
| GB (2) | GB623488A (en) |
| NL (1) | NL61894C (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE254421C (en) * | 1911-08-02 | |||
| DE518208C (en) * | 1929-06-15 | 1931-02-13 | I G Farbenindustrie Akt Ges | Process for the preparation of acylaminobenzolestibic acids |
| DE536996C (en) * | 1930-03-14 | 1931-10-29 | I G Farbenindustrie Akt Ges | Process for the production of arsic acids and stibic acids containing sulfur |
| GB458487A (en) * | 1935-06-17 | 1936-12-17 | George Malcolm Dyson | The preparation of new organic derivatives of antimony |
-
0
- NL NL61894D patent/NL61894C/xx active
-
1947
- 1947-04-23 CH CH255570D patent/CH255570A/en unknown
- 1947-05-02 GB GB11883/47A patent/GB623488A/en not_active Expired
- 1947-05-05 FR FR946090D patent/FR946090A/en not_active Expired
-
1949
- 1949-07-06 GB GB17826/49A patent/GB659250A/en not_active Expired
-
1950
- 1950-09-03 DE DEH5178A patent/DE890960C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE890960C (en) | 1953-09-24 |
| CH255570A (en) | 1948-06-30 |
| GB623488A (en) | 1949-05-18 |
| NL61894C (en) | |
| FR946090A (en) | 1949-05-23 |
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