GB377994A - Manufacture of arsenic compounds - Google Patents
Manufacture of arsenic compoundsInfo
- Publication number
- GB377994A GB377994A GB10098/31A GB1009831A GB377994A GB 377994 A GB377994 A GB 377994A GB 10098/31 A GB10098/31 A GB 10098/31A GB 1009831 A GB1009831 A GB 1009831A GB 377994 A GB377994 A GB 377994A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- mercaptobenzoxazole
- arsonic
- amino
- arsonic 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
- 150000001495 arsenic compounds Chemical class 0.000 title abstract 4
- 229940093920 gynecological arsenic compound Drugs 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 8
- 239000005864 Sulphur Substances 0.000 abstract 8
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 7
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical group O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 7
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 abstract 5
- 229950008475 oxophenarsine Drugs 0.000 abstract 5
- MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 229910000003 Lead carbonate Inorganic materials 0.000 abstract 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 150000001555 benzenes Chemical class 0.000 abstract 3
- 238000006396 nitration reaction Methods 0.000 abstract 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 2
- XBHVJGSWMGMRPZ-UHFFFAOYSA-N (7-amino-2-sulfanylidene-3H-1,3-benzoxazol-5-yl)arsonic acid Chemical compound NC1=CC(=CC=2N=C(OC21)S)[As](O)(=O)O XBHVJGSWMGMRPZ-UHFFFAOYSA-N 0.000 abstract 2
- QJXHWCWDIUPYPF-UHFFFAOYSA-N (7-chloro-2-sulfanylidene-1,3-dihydrobenzimidazol-4-yl)arsonic acid Chemical compound ClC1=CC=C(C2=C1N=C(N2)S)[As](O)(=O)O QJXHWCWDIUPYPF-UHFFFAOYSA-N 0.000 abstract 2
- LBPJAFJSUUQTLV-UHFFFAOYSA-N (7-chloro-2-sulfanylidene-3H-1,3-benzoxazol-5-yl)arsonic acid Chemical compound ClC1=CC(=CC=2N=C(OC21)S)[As](O)(=O)O LBPJAFJSUUQTLV-UHFFFAOYSA-N 0.000 abstract 2
- JEUVTJATJDARMA-UHFFFAOYSA-N 5-arsono-2-sulfanylidene-3H-1,3-benzoxazole-6-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=C1[As](O)(O)=O)N=C(S)O2 JEUVTJATJDARMA-UHFFFAOYSA-N 0.000 abstract 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 2
- -1 benzimidazole compound Chemical class 0.000 abstract 2
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 abstract 2
- 230000008030 elimination Effects 0.000 abstract 2
- 238000003379 elimination reaction Methods 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 239000001119 stannous chloride Substances 0.000 abstract 2
- 235000011150 stannous chloride Nutrition 0.000 abstract 2
- YARCNKWAIFQJDP-UHFFFAOYSA-N (3-amino-4-hydroxy-5-methoxyphenyl)arsonic acid Chemical compound COC1=C(O)C(N)=CC(=C1)[As](O)(O)=O YARCNKWAIFQJDP-UHFFFAOYSA-N 0.000 abstract 1
- QFLSPYZMAZLCQI-UHFFFAOYSA-N (3-amino-5-chloro-4-hydroxyphenyl)arsonic acid Chemical compound NC=1C(=C(C=C(C1)[As](O)(=O)O)Cl)O QFLSPYZMAZLCQI-UHFFFAOYSA-N 0.000 abstract 1
- KCXLTLYNFDGRKZ-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)arsonic acid Chemical compound O[As](O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 KCXLTLYNFDGRKZ-UHFFFAOYSA-N 0.000 abstract 1
- JRIGVWDKYXCHMG-UHFFFAOYSA-N (5-arsoroso-2-hydroxyphenyl)azanium;chloride Chemical compound Cl.NC1=CC([As]=O)=CC=C1O JRIGVWDKYXCHMG-UHFFFAOYSA-N 0.000 abstract 1
- VGIQSKSVZZRDKU-UHFFFAOYSA-N (7-acetamido-2-sulfanylidene-3H-1,3-benzoxazol-5-yl)arsonic acid Chemical compound C(C)(=O)NC1=CC(=CC=2N=C(OC21)S)[As](O)(=O)O VGIQSKSVZZRDKU-UHFFFAOYSA-N 0.000 abstract 1
- LCKPNEMDFIPHDC-UHFFFAOYSA-N (7-methoxy-2-sulfanylidene-3H-1,3-benzoxazol-5-yl)arsonic acid Chemical compound COC1=CC(=CC=2N=C(OC21)S)[As](O)(=O)O LCKPNEMDFIPHDC-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- MGPYBQTZLAZIPQ-UHFFFAOYSA-N 2-arsono-5-hydroxy-4-nitrobenzoic acid Chemical compound OC(=O)C1=C(C=C(C(O)=C1)[N+]([O-])=O)[As](O)(O)=O MGPYBQTZLAZIPQ-UHFFFAOYSA-N 0.000 abstract 1
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 abstract 1
- LPGKQQDXEJKVMD-UHFFFAOYSA-N 3-amino-5-arsono-2-hydroxybenzoic acid Chemical compound NC1=CC(=CC(C(O)=O)=C1O)[As](O)(O)=O LPGKQQDXEJKVMD-UHFFFAOYSA-N 0.000 abstract 1
- MCNBYOWWTITHIG-UHFFFAOYSA-N 4-amino-2-methoxyphenol Chemical compound COC1=CC(N)=CC=C1O MCNBYOWWTITHIG-UHFFFAOYSA-N 0.000 abstract 1
- AKNMLNVMQRXIPD-UHFFFAOYSA-N 5-arsono-2-sulfanylidene-3H-1,3-benzoxazole-7-carboxylic acid Chemical compound OC(=O)C1=CC(=CC2=C1OC(S)=N2)[As](O)(O)=O AKNMLNVMQRXIPD-UHFFFAOYSA-N 0.000 abstract 1
- ODNVNVBJCYOOHL-UHFFFAOYSA-N 7-iodo-3H-1,3-benzoxazole-2-thione Chemical compound IC1=CC=CC=2N=C(OC=21)S ODNVNVBJCYOOHL-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910000474 mercury oxide Inorganic materials 0.000 abstract 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- GPSSQIRGCXEBSH-UHFFFAOYSA-N oxoarsenic Chemical class [As]=O GPSSQIRGCXEBSH-UHFFFAOYSA-N 0.000 abstract 1
- 229960003742 phenol Drugs 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 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
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/80—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Arseno compounds are prepared by reducing, either alone or together with another arsenic compound of the benzene series, a benzoxazole or benzimidazole compound containing a mercapto group in the heterocyclic nucleus and an arsonic acid group with at least one other substituent in the benzene nucleus; or by condensing a corresponding trivalent arsenic compound with another such compound or with a trivalent arsenic compound of the benzene series. The products possess therapeutic properties. According to the examples, (1) 7-chloro-2-mercaptobenzoxazole-5-arsonic acid is reduced to the arseno compound with hydrosulphite; (2) 7-chloro-2-mercaptobenzimidazole-4-arsonic acid is reduced with hypophosphorous and hydriodic acids to the corresponding arseno compound; (3) 7 : 7<1>-diacetyl-amino-5 : 5<1>-arseno-2 : 2<1>-dimercaptobenzoxazole is prepared from the corresponding arsonic acid by reduction with hydrosulphite or stannous chloride; (4) arseno-(2-mercaptobenzoxazole-7-amino-5) -(3<1>-amino-4<1>-hydroxybenzene-1) is obtained by interaction of 7-amino-2-mercaptobenzoxazole-5-arsenoxide with 1-arsine-3-amino-4-hydroxybenzene; (5) 6-carboxyl-2-mercaptobenzoxazole-5-arsonic acid is reduced with hydrosulphite to the arseno compound; (6) 7 : 7<1>-dimethoxy-5 : 5<1>-arseno-2 : 2<1>-dimercaptobenzoxazole is prepared by the hydrosulphite reduction of the corresponding arsonic acid; (7) 2-mercaptobenzaxazole-5-sulphonic acid-7-arsonic acid is reduced to the arseno compound with hypophosphorous acid; (8) 7:7<1>-dicarboxyl-5 : 5<1> - arseno-2 : 2<1> - dimercaptobenzoxazole is prepared by the hydrosulphite reduction of the arsonic acid; (9) 7 : 7<1>-diiodo-5 : 5-arseno-2 : 2<1>-dimercaptobenzoxazole results from the interaction of 7-iodo-2-mercaptobenzoxazole-5-arsenoxide with the corresponding arsine; (10) 7-amino-2-mercaptobenzoxazole-5-arsonic acid and the corresponding arsenoxide are added with cooling to an alcoholic solution of stannous chloride, hydrochloric acid and hydriodic acid, when the arseno compound separates out. Arsonic acids. 7-Chloro-2-mercaptobenzoxazole-5-arsonic acid is prepared by treating 3-chloro-4-hydroxy - 5 - aminobenzene-1-arsonic acid with potassium xanthogenate and eliminating sulphur from the arsenic residue of the resulting 7-chloro - 2 - mercaptobenzoxazole-5-sulpharsonic acid by means of lead carbonate. 7-Chloro - 2 - mercaptobenzimidazole - 4 - arsonic acid is obtained from 3-nitro-4-chlorobenzene-1-arsonic acid by reduction, acylation e.g. acetylation of the amino product, nitration to give the 2-nitro compound, splitting off the acyl residue, reducing the nitro group, treating the diamino acid with potassium xanthogenate and removing sulphur from the arsenic residue of the 7-chloro-2-mercaptobenzimidazole-4-sulpharsonic acid formed. 7-Acetylamino-2-mercaptobenzoxazole-5-arsonic acid results from the nitration of 3-acetylamino-4-hydroxybenzene-1-arsonic acid, followed by reduction of the 5-nitro product, reaction of the amino acid with potassium xanthogenate and elimination of sulphur from the resulting sulpharsonic acid. 7-Amino-2-mercaptobenzoxazole-5-arsonic acid is obtained by saponification of the corresponding acetyl compound; it couples strongly with R-salt. 6-Carboxyl-2-mercaptobenzoxazole-5-arsonic acid is prepared by reducing 5-nitro-2-carboxyl - 4 - hydroxybenzene-1-arsonic acid, ring-closing the amino product with potassium xanthogenate and eliminating sulphur as before. 7-Methoxy-2-mercaptobenzoxazole-5-arsonic acid is formed when 3-methoxy-4-hydroxy-5-aminobenzene-1-arsonic acid, prepared by subjecting 1-amino-3-methoxy-4-hydroxybenzene to Bart's reaction p followed by nitration and reduction, is treated with potassium xanthogenate and the sulphur removed from the arsenic residue by means of lead carbonate. 2-Mercaptobenzoxazole-5-sulphonic acid-7-arsonic acid is prepared by converting 5-nitro-6-hydroxy-1-aminobenzene-3-sulphonic acid into the 1-arsonic acid by Bart's reaction, reducing to the 5-amino compound (which can couple with R-salt), and subjecting it to treatment with potassium xanthogenate and sulphur elimination as above. 7 - Carboxyl-2-mercaptobenzoxazole - 5 - arsonic acid is obtained from 1-amino-4-hydroxy-3-benzoic acid by subjecting it to Bart's reaction, nitrating and reducing, ring-closing the resulting 3-carboxyl-4-hydroxy - 5 - aminobenzene-1-arsonic acid with potassium xanthogenate and removing sulphur with lead carbonate. Arsenoxides. 7 - Iodo - 2 - mercaptobenzoxazole-5-arsenoxide is prepared from 3-nitro-4-hydroxybenzene-1-arsonic acid by first treating it with iodine in the presence of mercury oxide, reducing the resulting 5-iodo compound, ring-closing the product with potassium xanthogenate, eliminating sulphur by means of lead carbonate from the arsenic residue of the 7-iodo-2 - mercaptobenzoxazole - 5 - sulpharsonic acid formed, and reducing the product with sulphurous and hydriodic acids. 7-Amino-2-mercaptobenzoxazole-5-arsenoxide is obtained by reduction with sulphurous acid of the corresponding arsonic acid. Arsines. 7-Iodo - 2 - mercaptobenzoxazole-5-arsine is prepared by reduction of the corresponding arsonic acid by means of zinc dust and hydrochloric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10098/31A GB377994A (en) | 1931-04-02 | 1931-04-02 | Manufacture of arsenic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10098/31A GB377994A (en) | 1931-04-02 | 1931-04-02 | Manufacture of arsenic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB377994A true GB377994A (en) | 1932-08-02 |
Family
ID=9961447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10098/31A Expired GB377994A (en) | 1931-04-02 | 1931-04-02 | Manufacture of arsenic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB377994A (en) |
-
1931
- 1931-04-02 GB GB10098/31A patent/GB377994A/en not_active Expired
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