GB706421A - Improvements in or relating to process for preparing quaternary ammonium compounds - Google Patents
Improvements in or relating to process for preparing quaternary ammonium compoundsInfo
- Publication number
- GB706421A GB706421A GB8462/51A GB846251A GB706421A GB 706421 A GB706421 A GB 706421A GB 8462/51 A GB8462/51 A GB 8462/51A GB 846251 A GB846251 A GB 846251A GB 706421 A GB706421 A GB 706421A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluoromethyl
- chloroaceto
- chloroanilide
- chloride
- reacted
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0706421/IV (b)/1> where the alkyl radicals together contain 2-6 carbon atoms, Y and Z are hydrogen, halogen or trifluoromethyl (not both hydrogen) and X is one of the following linkages: -CH2-, -CH2-CO-NH-, -CH2-CH2-CO-NH-, -CH2-CH2-O-CO-NH-, -CH2-CH2-NH-SO2-, -CH2-CH2 CH2-NH-CO-, -CH2-CO-O-, -CH2-CO, or -CH2-CH2-NH-CO-NH-. These are made by treating chloracetamides of the formula Hal-CH2-CO-NH-C6H3Z(CF3) with secondary aliphatic amines to give substituted glycinamides and quaternating the latter with Hal-X-C6H3YZ. Ethyl acetate is the preferred solvent. An alternative method of preparation is from the above chloracetamides and (alkyl)2N-X-C6H3YZ. The quarternary halides may be converted into other salts, e.g. by double decomposition. In the examples, (1) dimethylaminoaceto-3- trifluoromethyl - 4 - chloranilide is reacted with 4-chlorobenzyl chloride, 3:4-dichlorobenzyl chloride, chloroaceto-3-trifluoromethyl-4-chloroanilide, 4-chlorophenacyl chloride, 4-chloro-phenylcarbamic b -chloroethyl ester, 3-trifluoromethyl-phenylcarbamic b -chloroethyl ester, chloroaceto-2-chloro-5-trifluoromethylanilide, chloroaceto-2:4:5-trichloroanilide and chloroacetic 3-methyl-4-chlorophenyl ester; (2) dimethylaminoaceto-3-trifluoromethylanilide is reacted with chloroaceto-4-chloroanilide and 3-trifluoromethyl-4-chlorophenylcarbamic b -chloroethyl ester; (3) dimethylaminoaceto - 3:5 - bis - trifluoromethyl - anilide is heated with 4-chlorobenzyl chloride and 3:4-dichlorobenzyl chloride; (4) diethylaminoaceto-3-trifluoromethyl-4-chloranilide is reacted with chloroaceto-3:4-dichloroanilide; (5) diethylaminoaceto-3-trifluoromethyl-anilide is reacted with chloroaceto-3-trifluoromethyl-4-chloroanilide; (6) chloroaceto-3-trifluoromethyl-4-chloroanilide is reacted with 4-chlorophenylcarbamic b -dimethylaminoethyl ester, 3-trifluoromethylphenylcarbamic b -dimethylaminoethyl ester, 1-dimethylamino-3-(31:41-dichlorobenzoylamino)-propane and N-(3:4 - dichlorophenyl)- N1 - (b - dimethylamino - ethyl)-urea; (7) chloroaceto-3-trifluoromethylanilide is reacted with 3-trifluoromethyl-4-chlorophenylcarbamic b -dimethylaminoethyl ester and N:N-dimethyl-N1-(3-trifluoromethyl-4-chlorobenzenesulphonyl) -ethylene diamine; (8) dimethylaminoaceto-2-chloro-5-trifluoromethylanilide is heated with chloroacetyl-4-chloroanilide and chloroacetyl-3-trifluoromethyl-4-chloroanilide; (9) dimethylaminoaceto-4-trifluoromethylanilide is reacted with 3:4-dichlorobenzyl chloride, chloroacetyl-3:4-dichloroanilide and chloroacetyl-3-trifluoromethyl-4-chloroanilide. Other products obtained similarly are those from diethylaminoaceto-3-trifluoromethyl-4-chloroanilide and the corresponding dipropylamino compound by reaction with chloroaceto-4-chloroanilide. The following amines are condensed first with chloroacetyl chloride to give chloroacetamides and then with dimethylamine to yield dimethylamino-acetamides: 3-trifluoromethyl-4-chloroaniline, 3-trifluoromethylaniline and 2-chloro-5-trifluoromethyl-aniline. N:N-dimethyl- N1 - (3-trifluoromethyl-4-chlorobenzenesulphonyl)-ethylene diamine is made from 3 - trifluoromethyl - 4 - chlorobenzenesulphonyl chloride and N:N-dimethyl-ethylenediamine. - Dimethylamino - 3 - (31: 41 - dichlorobenzoyl - amino)-propane is prepared from 3:4-dichlorobenzoyl chloride and 3-dimethylamino-propylamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH706421X | 1950-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB706421A true GB706421A (en) | 1954-03-31 |
Family
ID=4530416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8462/51A Expired GB706421A (en) | 1950-04-21 | 1951-04-11 | Improvements in or relating to process for preparing quaternary ammonium compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB706421A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774075A (en) * | 1980-06-06 | 1988-09-27 | L'oreal | Compositions containing bis-(quaternary ammonium) derivatives for the treatment of keratin materials and natural non-keratin materials or synthetic textile materials |
| CN108409614A (en) * | 2018-04-02 | 2018-08-17 | 成都联创蓉成医药科技有限公司 | A kind of amides compound, its pharmaceutical composition, Preparation method and use |
-
1951
- 1951-04-11 GB GB8462/51A patent/GB706421A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774075A (en) * | 1980-06-06 | 1988-09-27 | L'oreal | Compositions containing bis-(quaternary ammonium) derivatives for the treatment of keratin materials and natural non-keratin materials or synthetic textile materials |
| US4828819A (en) * | 1980-06-06 | 1989-05-09 | L'oreal | Compositions containing bis-(quaternary ammonium) derivatives for the treatment of keratin materials and natural non-keratin or synthetic textile materials |
| CN108409614A (en) * | 2018-04-02 | 2018-08-17 | 成都联创蓉成医药科技有限公司 | A kind of amides compound, its pharmaceutical composition, Preparation method and use |
| CN108409614B (en) * | 2018-04-02 | 2019-09-24 | 成都联创蓉成医药科技有限公司 | A kind of amides compound, its pharmaceutical composition, Preparation method and use |
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