Thionyl Chloride → 4,4-Dimethyl-2-(2-methyl-3-nitrophenyl)-4,5-dihydro-1,3-oxazole
Reaction equation
S(Cl)(Cl)=O.O[CH2:6][C:7]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=1[CH3:21])([CH3:9])[CH3:8]>C(OCC)C>[CH3:9][C:7]1([CH3:8])[CH2:6][O:22][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=2[CH3:21])=[N:10]1Participants
4
Procedure
Thionyl chloride, 37 ml, is added dropwise with stirring to 39.7 g (0.1575 mol) of N-(2-hydroxy-1,1-dimethylethyl)-2-methyl-3-nitrobenzamide. The mixture is allowed to stand overnight, poured into diethylether, filtered and the solvent evaporated to give 33.4 g of 4,5-dihydro-4,4-dimethyl-2-(2-methyl-3-nitrophenyl)oxazole as a pale yellow oil which crystallizes on cooling; mp 60°-61° C.