Aminoacetaldehyde dimethyl acetal → HCID 19699290, compound

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Reaction Conditions

Reaction Steps

A mixture of (-)-6,7-difluoro-2-isothiocyano-1,2,3,4-tetrahydronaphthalene (0.49 g, 2.2 mmol), prepared as in Example 10, and 2,2-dimethoxyethylamine (0.23 g, 2.2 mmol) in DMF was heated at 85° C. under argon for 2.5 hours. The solvent was removed under reduced pressure and the residue was dissolved in 2 to 3 mL of ethanol and 20 mL of 4N hydrochloric acid. The solution was heated at 85° C. for approximately 48 hours and cooled giving a crystalline material. The material was isolated by filtration and dried. Purification by column chromatography on silica gel (elution: 3% methanol/methylene chloride) gave (-)-6,7-difluoro-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0.225 g, 0.84 mmol), m.p. 200°-205° C. [α]D25 -77.9°, (c=0.6, 2:1 CHCl3 /CH3 OH).

Provenance & Evidence