Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-ca

Details Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-ca Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-ca

1978-11-08

1980-01-08

Randolph, John D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

424276, 549 30, 549 40, C07D32706

Patent

active

041827163

ABSTRACT:
This method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathiolane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathiolane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of a quaternary ammonium salt to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.

REFERENCES:
patent: 3005852 (1961-10-01), Freyermuth et al.
patent: 3006963 (1961-10-01), Buc et al.
patent: 3249499 (1966-05-01), Von Schmeling et al.
patent: 3393202 (1968-07-01), Kulkla et al.
patent: 3882237 (1975-05-01), Knight et al.
Djerassi et al., J. Am. Chem. Soc., vol. 75, pp. 3704-3708 (1953).
Janssen et al., J. Org. Chem., vol. 42, pp. 1530-1533 (1977).
Wilson, J. Am. Chem. Soc., vol. 87, pp. 3785-3786 (1965).
Breslow et al., Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part Two, pp. 816 to 825, Interscience Publishers, 1966 (NY).

Affiliated with

Also associated with

Rating

Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-ca does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-ca, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-ca will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1940969