GB672708A - New quaternary ammonium salts and processes for making the same - Google Patents
New quaternary ammonium salts and processes for making the sameInfo
- Publication number
- GB672708A GB672708A GB14021/49A GB1402149A GB672708A GB 672708 A GB672708 A GB 672708A GB 14021/49 A GB14021/49 A GB 14021/49A GB 1402149 A GB1402149 A GB 1402149A GB 672708 A GB672708 A GB 672708A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- alkyl
- ammonium
- methyl
- chlorophenyl
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises quaternary salts of the formula R(XCH2N+R1R2R3A-)n where X is O or S, R is aryl, R1 is alkyl, aralkyl or cycloalkyl, R2 and R3 are alkyl (1-4 carbon atoms), A is an inorganic or organic anion and n is 1 or 2; alternatively R1R2R3 and N may be the residue of a heterocyclic tertiary base such as pyridine or quinoline. These salts may be prepared by reacting halides R(XCH2Y)n, where Y is chlorine or bromine, with tertiary amines NR1R2R3, and if desired converting the resulting quaternary halides into other salts by known methods, e.g. double decomposition. A solvent may be used for the reaction and the temperature should be kept below 50 DEG C. R is preferably phenyl or naphthyl and may be substituted with cyano, nitro, halogen, alkyl or alkoxy groups (1-12 carbon atoms); R1, R2 and R3 may also carry inert substituents. In the examples, the following are prepared: (1) aryloxymethyldimethyl-benzyl-ammonium chlorides where aryl is phenyl, p-cyanophenyl, o- and p-nitrophenyl, p-bromophenyl, o- and p-chlorophenyl, 2 : 4-, 2 : 5-, 3 : 4- and 3 : 5-dichlorophenyl, 2 : 3 : 4- and 2 : 4 : 5-trichlorophenyl, o- and m - methyl - p - chlorophenyl, p - methyl - o-chlorophenyl, 3 : 5 - dimethyl - 4 - chlorophenyl and a - and b -naphthyl; also p-phenylene bis - (oxymethyl - dimethyl - benzyl - ammonium chloride); (2) aryloxymethyl-dimethyl-benzyl-ammonium picrates, where aryl is p-tolyl, p-anisyl, p-tert.-octylphenyl, m-chlorophenyl, m-chloro-p-methylphenyl and p-chloro-o- and m-anisyl; (3) o-chlorophenoxy-, 2 : 4-dichlorophenoxy- and b -naphthoxy-methyl-triethyl-ammonium chlorides; (4) p-anisyloxymethyl - trimethyl - ammonium picrate, which is reconverted into the chloride; (5) p-nitrophenoxy-, 2 : 4-dichlorophenoxy-and 3-methyl-4 - chlorophenoxy - methyl - pyridinium chlorides; (6) 2 : 4-dichlorophenoxymethyl-quinolinium chloride; (7) 3 : 5-dimethyl-4-chlorophenoxymethyl - dimethyl - alkyl - ammonium chlorides, where alkyl is n-amyl, n-hexyl, isooctyl, n-decyl, lauryl, cetyl and stearyl; (8) 2 : 4 - dichloro - phenoxymethyl - dimethyl-alkyl-ammonium chlorides, where alkyl is n-octyl, n-decyl and stearyl; (9) o-nitro-p-chlorophenoxymethyl - dimethyl - n - octyl - ammonium chloride; (10) 3 : 5-dimethyl-4-chlorophenoxymethyl - dimethyl - cyclo - octyl-ammonium chloride; (11) p-phenylene bis-(oxymethyl - dimethyl - alkyl - ammonium chlorides), where alkyl is n-amyl, n-hexyl, n-octyl and stearyl; (12) 4-chloro- and 2 : 5-dichloro - phenylthiomethyl - dimethyl - n-octyl- and n-decyl-ammonium chlorides; (13) p-chloro-, p-methyl-, 2 : 4-, 3 : 4- and 2 : 5-dichloro - phenylthiomethyl - dimethyl - benzyl-ammonium chlorides, and the picrate of the last named. The Provisional Specification refers also to compounds of the above general formula where R is aralkyl (X = S only). A further method is given of preparing the quaternary salts, viz. reaction of NR1R2R3 with R(XCH2SO3Z)n, where Z is alkyl, aryl, aralkyl or cycloalkyl; this gives a quaternary ammonium sulphonate which may if desired be converted into other salts. It is also stated that n may be 2. The aryloxymethyl and arylthiomethyl halides may be made as in Specification 647,215. Specification 434,602 also is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB14021/49A GB672708A (en) | 1949-05-25 | 1949-05-25 | New quaternary ammonium salts and processes for making the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB14021/49A GB672708A (en) | 1949-05-25 | 1949-05-25 | New quaternary ammonium salts and processes for making the same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB672708A true GB672708A (en) | 1952-05-28 |
Family
ID=10033542
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB14021/49A Expired GB672708A (en) | 1949-05-25 | 1949-05-25 | New quaternary ammonium salts and processes for making the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB672708A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734918A (en) * | 1956-02-14 | Quaternary salts of chlorphenoxy | ||
US2918401A (en) * | 1956-03-29 | 1959-12-22 | Burroughs Wellcome Co | Treatment of nematodes with quaternary ammonium compounds |
US3929886A (en) * | 1969-03-18 | 1975-12-30 | Ugine Kuhlmann | Quaternary ammonia salts of polyhalogenated aromatic compounds |
-
1949
- 1949-05-25 GB GB14021/49A patent/GB672708A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734918A (en) * | 1956-02-14 | Quaternary salts of chlorphenoxy | ||
US2918401A (en) * | 1956-03-29 | 1959-12-22 | Burroughs Wellcome Co | Treatment of nematodes with quaternary ammonium compounds |
US3929886A (en) * | 1969-03-18 | 1975-12-30 | Ugine Kuhlmann | Quaternary ammonia salts of polyhalogenated aromatic compounds |
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