Production of compounds containing sulfur and nitrogen

    公开(公告)号:GB1004660A

    公开(公告)日:1965-09-15

    申请号:GB1279664

    申请日:1964-03-26

    Applicant: BASF AG

    Abstract: The invention comprises compounds of the general formula in which R is an unsubstituted or halogensubstituted substituted alkyl, aryl (including alkaryl), aralkyl or cycloalkyl radical, R1 and R2 are alkyl radicals and R1 is a hydrogen atom or an amide group of the formula the radical R is as defined above and may bear one or two halogen atoms such as Cl or Br atoms. They may be obtained by reacting an isocyanate of the formula R-N = C = O, or a substance which will form such an isocyanate under the reaction conditions with an oxosulphoniumylide of the formula if desired in the presence of an inert solvent, at a temperature of from - 10 DEG C. to 100 DEG C. Suitable isocyanates are phenyl, p-tolyl, benzyl, methyl, ethyl, isopropyl, n-butyl, n-octadecyl, cyclohexyl, cyclododecyl, p - chlorophenyl, o-chlorophenyl, 4 - chloro - 3 - methylphenyl, 2-methyl cyclohexyl and b - chloroethyl isocyanates. The equivalent carbamyl chlorides e.g. those formed by reaction of a primary amine with phosgene, may be used instead of isocyanates. Suitable solvents are for example ethers, hydrocarbons, chlorohydrocarbons, N,N - dialkylsubstituted amides or lower fatty acids, N-alkyllactams or dialkyl sulphoxides. The products depend on the amounts of reactants used i.e. if an ylide is reacted with an isocyanate in the molar ratio of 0.5: 1 a substituted malonamide is obtained, but if the molar ratio is 1: 1 or an excess of isocyanate is used a mixture of the mono- and di-addition products is formed. The products are useful as intermediates for pharmaceuticals, dyes and pesticides. Malonic dianilide, p-chloroacetanilide, acetanilide, malonic acid-N,N1-butyldiamide and malonic acid-N,N1-isopropyl-diamide respectively are prepared by catalytic desulphurization with Raney nickel of the appropriate substituted oxosulphurylene amide.

    Improvements in the production of omega-aminododecane acidlactam, and a new intermediate compound therein

    公开(公告)号:GB873257A

    公开(公告)日:1961-07-19

    申请号:GB1832959

    申请日:1959-05-29

    Applicant: BASF AG

    Abstract: o -Aminododecane acid lactam is obtained by treating cyclododecane in dissolved form at a temperature of -30 to +40 DEG C. under the action of light with hydrogen chloride and a nitrosating agent, separating the resulting cyclododecanone oxime hydrochloride, treating it at 80-150 DEG C. with an acid or acid chloride known for the Beckmann rearrangement and separating the o -aminododecane acid lactam by introducing the resulting rearrangement mixture into water. Cyclododecanone oxime hydrochloride is claimed per se; it may be obtained in solid or liquid forms. Specified nitrosating agents are nitrosyl chloride, which may be prepared in situ, e.g. from an alkyl nitrite and hydrogen chloride, and a mixture of chlorine and nitrogen monoxide. The initial cyclododecane solution preferably contains 0.5 to 5% by weight of by-products formed by the nitrosation of cyclododecane. Specified Beckmann rearrangement agents are sulphuric acid, oleum, chlorsulphonic acid, phosphorus pentachloride and benzene-sulphonyl chloride. o -aminododecane acid lactam, e.g. 1-10% based on sulphuric acid, is preferably added to the mixture to be subjected to rearrangement. The cyclododecanone oxime hydrochloride may be converted to the free oxime by digestion with water or by precipitation from an alcoholic solution of the hydrochloride by means of water. o -aminododecane acid lactam may be used in polyamide preparation; it may be converted to o -aminododecane carboxylic acid or its hydrochlorides by boiling with concentrated HCI.

Patent Agency Ranking