p-(1,1,2,2-Tetrafluoroethoxy)benzaldehyde oxime → 4-Chloro-benzaldehyde oxime

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Using a similar procedure, 1-amino-3-p{[p-(1,1,2,2-tetrafluoroethoxy)benzylidene]amino}guanidine hydrochloride (white solid, mp 205°-212° C.); 1-amino-3-{p-(trifluoroethoxy)benzylidene]amino}guanidine hydrochloride (white powder; mp 235°-238° C.); and 1-amino-3-(p-chlorobenzylideneamino)guanidine hydrochloride may be prepared. The second products of the reactions, p-(1,1,2,2-tetrafluoroethoxy)benzaldehyde oxime (pinkish white solid, mp 47°-53.5° C.); α,α,α-trifluoro-p-anilaldehyde oxime (off-white solid, mp 46°-49.5° C.) and p-chlorbenzaldehyde oxime may also be isolated from the reactions.

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