GB362852A - Improved manufacture of organic arsenic compounds - Google Patents
Improved manufacture of organic arsenic compoundsInfo
- Publication number
- GB362852A GB362852A GB26265/30A GB2626530A GB362852A GB 362852 A GB362852 A GB 362852A GB 26265/30 A GB26265/30 A GB 26265/30A GB 2626530 A GB2626530 A GB 2626530A GB 362852 A GB362852 A GB 362852A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- arsonic acid
- arsonic
- aromatic
- ethyl
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001495 arsenic compounds Chemical class 0.000 title 1
- 229940093920 gynecological arsenic compound Drugs 0.000 title 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 4
- ONNMHQZTPSTJNG-UHFFFAOYSA-N [4-[(3-ethoxy-3-oxopropanoyl)amino]phenyl]arsonic acid Chemical compound [As](=O)(O)(O)C1=CC=C(NC(CC(=O)OCC)=O)C=C1 ONNMHQZTPSTJNG-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- NCXGLCHXHAUCDV-UHFFFAOYSA-N 4-(4-arsonoanilino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC1=CC=C([As](O)(O)=O)C=C1 NCXGLCHXHAUCDV-UHFFFAOYSA-N 0.000 abstract 3
- OUFRIWNNMFWZTM-UHFFFAOYSA-M sodium arsanilate Chemical compound [Na+].NC1=CC=C([As](O)([O-])=O)C=C1 OUFRIWNNMFWZTM-UHFFFAOYSA-M 0.000 abstract 3
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- MYMNBFURSYZQBR-UHFFFAOYSA-N 5-ethoxy-5-oxopentanoic acid Chemical compound CCOC(=O)CCCC(O)=O MYMNBFURSYZQBR-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- LFTKTRUQKFFBFQ-UHFFFAOYSA-N [4-[(5-ethoxy-5-oxopentanoyl)amino]phenyl]arsonic acid Chemical compound [As](=O)(O)(O)C1=CC=C(NC(CCCC(=O)OCC)=O)C=C1 LFTKTRUQKFFBFQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- MIHQXWXJCPUUCU-UHFFFAOYSA-N aminoarsonic acid Chemical class N[As](O)(O)=O MIHQXWXJCPUUCU-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- KWFADUNOPOSMIJ-UHFFFAOYSA-N ethyl 3-chloro-3-oxopropanoate Chemical compound CCOC(=O)CC(Cl)=O KWFADUNOPOSMIJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 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
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Derivatives of aromatic p-aminoarsonic acids, containing the group .NH.CO.X.CO.N:, in which X is an aliphatic bivalent radical, and in which one or both of the free valencies of the right-hand nitrogen atom may be satisfied by hydrogen or by a simple or substituted aliphatic, aromatic, hydroaromatic or heterocyclic radical or radicals, or in which the nitrogen atom forms part of a heterocyclic ring, are manufactured by condensing the aromatic p-arsonic acid or a derivative thereof with an aliphatic dicarboxylic acid or a simple derivative thereof, such as an ester, anhydride or acid chloride, and condensing the product or a simple derivative thereof with ammonia or with a primary or secondary amine having a simple or substituted aliphatic, aromatic, hydroaromatic or heterocyclic radical or radicals, or with a secondary heterocyclic nitrogenous base. In examples: (1) sodium p-arsanilate is heated with succinic anhydride, yielding, on acidification, p-arsonosuccinanilic acid, which is condensed with aniline to produce succinanilide-mono-p-arsonic acid; (2) p-arsonosuccinanilic acid is condensed with methylamine or ethylamine, producing succinanilomethylamine-p-arsonic acid or the corresponding ethylamide; (3) p-arsonosuccinanilic acid is converted by heat into succinanil-p-arsonic acid, which with alcoholic ammonia yields succinanilamide-p-arsonic acid; (4) succinanil-p-arsonic acid with dimethylamine produces succinanilodimethylamide-p-arsonic acid; (5) succinanil-p-arsonic acid is condensed with piperidine to form succinanilopiperidide-p-arsonic acid; (6) sodium p-arsanilate is treated with carbethoxyacetyl chloride and caustic soda to produce ethyl p-arsonomalonanilate which is heated under pressure with aqueous ammonia giving malonanilamide-p-arsonic acid; (7) ethyl p-arsonomalonanilate is treated with methylamine or ethylamine to produce malonanilomethylamide-p-arsonic acid or the corresponding ethylamide; (8) ethyl p-arsonomalonanilate with dimethylamine yields malonanilodimethylamide-p-arsonic acid; (9) ethyl-p-arsonomalonanilate is saponified and the product treated with thionyl chloride followed by aniline to produce malonanilide-p-arsine oxide, which is converted by hydrogen peroxide to malonanilide-p-arsonic acid; (10) sodium p-arsanilate is treated with caustic soda and g -carbethoxybutyryl chloride (obtained by treating monoethyl glutarate with thionyl chloride), producing ethyl p-arsonoglutaranilate, which with methylamine yields glutaranilomethylamide-p-arsonic acid. The Provisional Specification describes the treatment of aminoarsonic acids in general, and the manufacture of compounds containing the group .NH.CO.CO.N : or the group .NH.CO.X.CO.N : in which X may be an aromatic, hydroaromatic or heterocyclic bivalent radical.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26265/30A GB362852A (en) | 1930-09-03 | 1930-09-03 | Improved manufacture of organic arsenic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26265/30A GB362852A (en) | 1930-09-03 | 1930-09-03 | Improved manufacture of organic arsenic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB362852A true GB362852A (en) | 1931-12-03 |
Family
ID=10240922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26265/30A Expired GB362852A (en) | 1930-09-03 | 1930-09-03 | Improved manufacture of organic arsenic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB362852A (en) |
-
1930
- 1930-09-03 GB GB26265/30A patent/GB362852A/en not_active Expired
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