Process for the production of organic nitrogen compounds containing the imide-chloride group

摘要

Organic compounds containing a grouping are prepared by reacting a compound of formula R1R2R3N (where R1 and R2 are alkyl, aryl or heterocyclic radicals which may be substituted by halogen, cyano, aryl, alkyl, nitro, amino or imino, or R1 and R2 form a heterocyclic ring with the nitrogen, and R3 is alkyl or substituted alkyl or is linked with R1 and R2 to form a heterocyclic system) or a hydrohalide or quaternary ammonium derivative thereof, with chlorine below 140 DEG C. to the extent that in the subsequent chlorination, dissociation, condensation and polymerization reactions are avoided, and then treating the product with chlorine at 140-300 DEG C., whereby alkyl or substituted alkyl chloride is split off to leave the compound. Solvents may be employed. Examples prepare (1) Cl2C : N.CCl2.CCl2.N : CCl2 from (CH3)2NCH2CH2N(CH3)2, (3) Cl3C.N : CCl2 from (CH3)3N.HCl, (4) Cl3C.CCl2.N : CCl2 from (CH3)2NCH2CH2Cl.HCl, (5) trichlorophenyl isocyanide dichloride from phenyltrimethylammonium chloride, (6) tetrachloropyrazine from N,N1 - dimethylpiperazine, (7) tetrachloropyrazine from N,N1-bis-(ethanol) piperazine, (8) tetra- and pentachloropyridine from N-methylpiperidine, (9) trichlorophenyl isocyanide dichloride from dimethylaniline, from C6Cl5N(CH3)2, from (the latter obtained from trichlorophenyl isocyanide, dichloride and dimethylamine), from o-dimethylaminotoluene from 2,5 - bis - (dimethylamino) - 3,6 - dichloro-p-benzoquinone, and (16 Cl2C:N.CCl2.CCl2.CCl2.COCl from N-methylpyrrolidone. Other starting materials are listed. Specification 1,011,555 is referred to.ALSO:Examples of a process for the production of organic compounds containing the grouping (see Division C2) include the production by chlorination of (2) cyanuric chloride from hexamethylene tetramine; from 2-dimethylamino-4,6-dichlorotriazine, and from 2,4-bis-(dimethylamino)-6-chlorotriazine. Specification 1,011,555 is referred to.ALSO:A nematocidal composition comprises 1% of 2, 4, 6-trichlorophenyl isocyanide dichloride in admixture with talcum. Specification 1,011,555 is referred to.