Water → 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A flask was charged with 30.2 g of a 50% solution of dibutylaminosulfenyl chloride (0.077 mole) in hexane and 15.8 g of 98% 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (0.07 mole) was added. Triethylamine (7.8 g, 0.077 mole) was added to the mixture with agitation over a period of seven minutes. A temperature rise from 24.5° to 26° C. was observed. A portion (1.9 g, 0.0115 mole) of the triethylamine/sulfur dioxide catalyst prepared in Example 3 was added dropwise. The temperature gradually rose to 30° C., and was raised further by external heating to 35° C. for a total reaction time of 100 minutes from the beginning of triethylamine addition. Twenty minutes later the mixture was cooled to 11° C. and 31 ml of water was added and mixed. The mixture was filtered to remove a small amount of solid, separated, and the organic layer was concentrated to yield 26.64 g of 90% (hplc) 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (dibutylaminothio)methylcarbamate (a 90% chemical yield based on the starting carbamate).

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