Ethyl Acetate → phenyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]-2-methyl-propiothioimidate

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Reaction Steps

To a solution of phenyl N-[[methyl[fluorocarbonyl]amino]thio]-2-methylpropiothioimidate (7.8 g, 27 mmoles) as prepared in Preparation 1 and cetylbenzyldimethylammonium chloride (0.9 g) in methylene chloride (150 ml) is added a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranol (4.5 g, 27 mmoles) in 0.18N sodium hydroxide (150 ml). The two-phase reaction mixture is stirred vigorously at ambient temperature for 90 minutes. The layers are separated and the organic phase dried over anhydrous sodium sulfate. Removal of the solvent gives a clear brown oil. This material is transferred to a column of silica gel and the chromatogram developed with a solvent mixture consisting of 8% ethylacetate in Skellysolve B. From the appropriate fraction there is obtained a white solid which is recrystallized from hexane to give the product phenyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7- benzofuranyl]oxy]carbonyl]amino]thio]-2-methyl-propiothioimidate as a white crystalline solid, mp 104°-106°.

Provenance & Evidence