Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-12-09
1989-10-31
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
564 29, C07D27718
Patent
active
048778800
ABSTRACT:
A process for the preparation of certain iminothiazolidines of the formula ##STR1## in which R is halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, pentahalomethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy, methylsulfonyl, C.sub.1 -C.sub.4 alkyloxyiminomethyl, benzyloxyiminomethyl, 1-(C.sub.1 -C.sub.4)alkyl oxyiminoethyl or 1-benzyloxyiminoethyl; R.sub.1 is hydrogen or halo; R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; and R.sub.3 and R.sub.4 are independently hydrogen, halo, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 fluoroalkoxy or C.sub.1 -C.sub.4 alkylthio, by reacting a thiourea with methanesulfonic acid or trifluoromethanesulfonic acid in an aprotic solvent for a period of time and at a temperature sufficient to achieve cyclization of the thiourea to form said iminothiazolidine.
The thiourea may be prepared by reaction of an N-3-substituted allyl aniline with an arylisothiocyanate.
REFERENCES:
patent: 3804848 (1974-04-01), Behner
patent: 4326876 (1982-04-01), Aoyagi
Dains et al., JACS, vol. 44, pp. 2637-2643.
Cholpankulova et al., Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 1984 (6), pp. 75-81.
Ackerman Joel G.
Gerstl Robert
ICI Americas Inc.
Martin Paul R.
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