THERAPEUTISCHE VERBINDUNGEN

1429852 Amides WELLCOME FOUNDATION Ltd 23 Feb 1973 [25 Feb 1972 28 Feb 1972] 8920/73 Addition to 1380882 Heading C2C [Also in Division A5] The invention comprises amides of the formula wherein L is -Z-A-Z-, where Z is when m is 0 or 1 and X 2 , X 3 and X 4 are H or C 1-3 alkyl; and A is -O.CO.O- or a divalent radical of a dicarboxylic or monocarboxylic acid containing 2 to 14 carbon atoms and having respectively two ester linkages or one ester and one other linkage, to the rest of the molecule, or -CH 2 -, -(CH 2 ) 2 -, or where X and X 1 are H or C 1-3 alkyl ; R and R1 are H, optionally substituted saturated aliphatic hydrocarbon group having 1 to 7 carbon atoms or an unsaturated aliphatic hydrocarbon group having 2 to 4 carbon atoms; R2 and R3 are H, C 1-4 alkyl, R5CO, R6CO where R5 and R6 are H, optionally substituted aliphatic C 1-7 hydrocarbyl, or unsaturated aliphatic C 2-4 hydrocarbyl or together with R and R1 respectively form C 2-4 alkylene, provided that when L is other than -Z-A-Z- at least one of R2 and R3 is, as appropriate, the group R5CO or R6CO and when one or more of the groups R, R1, R5 and R6 is a saturated aliphatic C 1-7 hydrocarbyl group substituted by NH 2 , C 1-4 alkylamino or di-(C 1-4 alkyl) amino, acid addition salts thereof. The compounds are obtained by one of the following methods:- (a) reacting in liquid mediums compounds of the Formula III wherein Alk is an alkali metal, D is R or R1 and E is R2 or R3 with compounds of the Formula IV where B is a reactive nucleophilic group or atom; (b) acylating amines of the Formula V wherein at least one of T1, T2, T3 and T4 is H and otherwise T1 and T2 are R1CO or RCO and T3 and T4 are R2 and R3 respectively; or (c) reacting in liquid medium compounds of the Formula VII where D is R or R1 and E is R2 or R3 and P is H or an alkali metal with compounds of the Formula VIII wherein G is the moiety of the group A that interconnects the two terminal oxygen atoms thereof. 41-(2-Hydroxyethoxy)acetanilide is made by reacting 4-acetamidophenol with 2-chloroethanol.