GB408638A - Improvements in or relating to the production of aromatic thio-acyl-amides - Google Patents
Improvements in or relating to the production of aromatic thio-acyl-amidesInfo
- Publication number
- GB408638A GB408638A GB2786232A GB2786232A GB408638A GB 408638 A GB408638 A GB 408638A GB 2786232 A GB2786232 A GB 2786232A GB 2786232 A GB2786232 A GB 2786232A GB 408638 A GB408638 A GB 408638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl
- thioacylamides
- treatment
- hydrogen sulphide
- phosphorus
- 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
- 125000003118 aryl group Chemical group 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 3
- 239000012442 inert solvent Substances 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 abstract 1
- UPTOWXNJLZJTGD-UHFFFAOYSA-N 1,4-dimethoxy-2-nitrobenzene Chemical compound COC1=CC=C(OC)C([N+]([O-])=O)=C1 UPTOWXNJLZJTGD-UHFFFAOYSA-N 0.000 abstract 1
- YRTUCZUPMWNTNY-UHFFFAOYSA-N 1-(1-aminonaphthalen-2-yl)ethanone Chemical compound C1=CC=CC2=C(N)C(C(=O)C)=CC=C21 YRTUCZUPMWNTNY-UHFFFAOYSA-N 0.000 abstract 1
- CZIHNRWJTSTCEX-UHFFFAOYSA-N 2 Acetylaminofluorene Chemical compound C1=CC=C2C3=CC=C(NC(=O)C)C=C3CC2=C1 CZIHNRWJTSTCEX-UHFFFAOYSA-N 0.000 abstract 1
- CZVHCFKUXGRABC-UHFFFAOYSA-N N,N'-Diacetylbenzidine Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(NC(C)=O)C=C1 CZVHCFKUXGRABC-UHFFFAOYSA-N 0.000 abstract 1
- FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 abstract 1
- UCMKOQLLXBURAV-UHFFFAOYSA-N N-(3-amino-4-methylnaphthalen-1-yl)acetamide Chemical compound C(C)(=O)NC1=CC(=C(C2=CC=CC=C12)C)N UCMKOQLLXBURAV-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- XVAIDCNLVLTVFM-UHFFFAOYSA-N methacetin Chemical compound COC1=CC=C(NC(C)=O)C=C1 XVAIDCNLVLTVFM-UHFFFAOYSA-N 0.000 abstract 1
- RXRZTIATQMVXOK-UHFFFAOYSA-N n-(1,2-dihydroacenaphthylen-5-yl)acetamide Chemical compound C1CC2=CC=CC3=C2C1=CC=C3NC(=O)C RXRZTIATQMVXOK-UHFFFAOYSA-N 0.000 abstract 1
- HOZRMSVNIKYCMB-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC=C(OC)C(NC(C)=O)=C1 HOZRMSVNIKYCMB-UHFFFAOYSA-N 0.000 abstract 1
- JZNFUSIATBNRFI-UHFFFAOYSA-N n-(2-ethoxynaphthalen-1-yl)acetamide Chemical compound C1=CC=CC2=C(NC(C)=O)C(OCC)=CC=C21 JZNFUSIATBNRFI-UHFFFAOYSA-N 0.000 abstract 1
- KFTYNYHJHKCRKU-UHFFFAOYSA-N n-(3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1 KFTYNYHJHKCRKU-UHFFFAOYSA-N 0.000 abstract 1
- RNGWVUMBRKJTDR-UHFFFAOYSA-N n-phenanthren-1-ylacetamide Chemical compound C1=CC2=CC=CC=C2C2=C1C(NC(=O)C)=CC=C2 RNGWVUMBRKJTDR-UHFFFAOYSA-N 0.000 abstract 1
- 229960003893 phenacetin Drugs 0.000 abstract 1
- -1 phosphorus halogen compound Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aromatic thioacylamides wherein the acyl group is aliphatic are prepared by treating in the absence of water the acyl derivative of an aromatic amine with a phosphorus halogen compound wherein the phosphorus is pentavalent, and treating the products without isolation with hydrogen sulphide in the presence of an inert solvent to form the corresponding thioacylamides. Suitable inert solvents are ether, benzene, carbon tetrachloride or chloroform, and the treatment with hydrogen sulphide is advantageously carried out with cooling of the reaction mixture. When the starting materials contain other reactive groups such as hydroxy or amino these are first protected by treatment with a toluenesulphonamide. In examples, the following acylamides are converted to thioacylamides by treatment with phosphorus pentachloride followed by hydrogen sulphide, the inert solvent being benzene and cooling of the reaction mixture being specified in some cases:--phenacetin, acetyl-p-anisidine, acetyl-o-toluidide, acetyl-m-xylidine, acetamidohydroquinone dimethylether (reduction and acetylation of nitrohydroquinone dimethylether), 5-acetylaminotrimethylpyrogallol, m-nitroacetanilide, 1.3- and 1.4-diacetylphenylenediamines, diacetylbenzidine, propionanilide, 2-acetylnaphthylamine, 4-acetylamino-1-methyl-naphthylamine, 4-acetylaminonaphthyl-methyl-and ethyl-ethers, 1-acetylamino-2-naphthyl ethyl ether, 2-acetylaminofluorene, 2-acetylaminodiphenyleneoxide, 5 - acetylaminoacenaphthene. The conversion of acetyl - o - anisidine, acetylaminophenanthrene, and 1-alkoxy - 2 - acetylaminonaphthalene is also mentioned. The products are useful for conversion to thiazole and thence to cyanine dyes Specifications 322,184, [Class 2 (iii)], and 351,557 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2786232A GB408638A (en) | 1932-10-06 | 1932-10-06 | Improvements in or relating to the production of aromatic thio-acyl-amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2786232A GB408638A (en) | 1932-10-06 | 1932-10-06 | Improvements in or relating to the production of aromatic thio-acyl-amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB408638A true GB408638A (en) | 1934-04-06 |
Family
ID=10266509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2786232A Expired GB408638A (en) | 1932-10-06 | 1932-10-06 | Improvements in or relating to the production of aromatic thio-acyl-amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB408638A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213076A (en) * | 1962-04-19 | 1965-10-19 | Archer Daniels Midland Co | Sulfurization of schiff base |
-
1932
- 1932-10-06 GB GB2786232A patent/GB408638A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213076A (en) * | 1962-04-19 | 1965-10-19 | Archer Daniels Midland Co | Sulfurization of schiff base |
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