Preparation of omega-substituted alkanamide
AssigneeEastman Kodak Company
InventorPaul R. Buckland
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Abstract
A method for the preparation of omega-arylthioalkanamides, especially omega-imidazolylthioalkanamides useful, for example, in the preparation of certain antihypercholesterolemic agents is disclosed. The method involves three steps including an addition reaction between a lactone and an amine to produce an omega-hydroxyalkanamide; a condensation reaction between said omega-hydroxyalkanamide and an alkanesulfonic acid halide or anhydride to produce an alkanesulfonate ester; reaction of said alkanesulfonate ester with a salt of an aromatic mercaptan, especially an imidazole-2-thiol, to produce the omega-imidazolylthioalkanamides.
Claims3
A process for preparing an omega-substituted arylthioalkanamide of the formula
- ArS--Y--CONR.sup.8 R.sup.9,
- wherein
- Ar is 4,5-diphenyl-1H-imidazol-2-yl;
- Y is selected from the group consisting of trimethylene, tetramethylene, or pentamethylene, or trimethylene, tetramethylene, or pentamethylene substituted by a group selected from the list consisting of methyl, ethyl, propyl, or butyl;
- R.sup.8 and R.sup.9 each independently represents hydrogen, C.sub.1 -C.sub.7 alkyl, phenyl optionally substituted with 1-3 groups selected from C.sub.1 -C.sub.4 alkyl or alkoxy, F, Br, OH, CN, CO.sub.2 H, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 carbalkoxy, NR.sup.10 R.sup.10, NCOR.sup.11, and furfuryl, with the proviso that R.sup.8 and R.sup.9 cannot both be aromatic;
- R.sup.10 is C.sub.1 -C.sub.4 alkyl;
- and R.sup.11 is H or C.sub.1 -C.sub.4 alkyl;
- which comprises the steps:
- (a) reacting delta valerolactone with an amine of the formula R.sup.8 R.sup.9 NH, to provide a compound of the formula
- HO--Y--CONR.sup.8 R.sup.9 ;
- followed by
- (b) treatment with a compound of the formula R.sup.7 SO.sub.2 X, wherein R.sup.7 is a lower alkyl group of 1-4 carbon atoms, or trifluoromethyl;
- and X is an anion selected from the group consisting of --F, --Cl, and --Br;
- to provide a compound of the formula
- R.sup.7 SO.sub.2 O--Y--CONR.sup.8 R.sup.9 ;
- followed by
- (c) treatment with a compound of the formula ArSH in the presence of a non-nucleophilic base.
Dependencies are inferred from the claim text.