Bromine → 2-Bromo-1-(4-cyclohexylphenyl)ethanone

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Reaction Steps

p-cyclohexylphenyl methyl ketone is reacted with bromine in a non-polar solvent to produce the corresponding p-cyclohexylphenacyl bromide. Reaction of this reactive alpha-bromo ketone with commercially available thioacetamide in an protic solvent such as methanol with heat affords the corresponding 2-methyl-4-(4-cyclohexylphenylthiazole. N-Alkylation of this thiazole with [methoxy(polyethylene)n-1]ethyl chloride (where n is from 19 to 24) in aprotic solvents such as dimethylformamide and heat readily forms the corresponding methochioride product, which is also named either N-[methoxy(polyethylene)n-1]ethyl-2-methyl-4-(4-cyclohexylphenypthiazolium chloride or 3-[methoxy(polyethylene)n-1]ethyl-2-methyl-4-(4-cyclohexylphenyl)thiazolium chloride. Reaction of this thiazolium chloride with (N,N-dimethyl)amino benzaldehyde in a protic solvent such as methanol with a basic catalyst such as piperidine and heat then produces the desired 4-(4-cyclohexylphenyl)-2-(N,N-diethylaminostyryl)-3-[methoxy(polyethylene)n-1]ethylthiazolinm chloride, which can also be named 4-(4-cyclohexylphenyl)-2-[2-(4-dimethylaminophenyl)vinyl]-3-[methoxy(polyethylene)n-1]ethylthiazol-3-ium chloride. In all of the above reactions n is from 19 to 24.

Provenance & Evidence