Carbofuran → Carbamic acid, methyl(phenylthio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

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Reaction Steps

A solution of 11 g of carbofuran in 50 ml of pyridine was added to 14.5 g of benzenesulfenyl chloride and the mixture was allowed to stand overnight at room temperature. The mixture was filtered, 250 ml of dry ether was added to the filtrate and the mixture refiltered. The filtrate was concentrated under reduced pressure. The residue was washed by stirring with 50 ml of water for one hour at room temperature. When the oily product was stirred with 200 ml of hexane, about 80% dissolved. The hexane solution was decanted, washed six times with water, then with saturated aqueous sodium chloride solution, then dried over sodium sulfate. The dried solution was concentrated under reduced pressure and the residue distilled to give a colorless liquid, b.p. 168°-174° at 0.005 mm. Redistillation gave 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(phenylthio)carbamate, b.p. 168° at 0.005 mm, nD25 1.5758. This compound crystallized upon standing, m.p. 66°. The n.m.r. spectrum was consistent with the assigned structure.

Provenance & Evidence