Formanilide → HCID 11126692, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-1-(chloromethylthio)benzene (21 mmol) was added to a mixture of formanilide (21 mmol) and potassium tert-butoxide (21 mmol) in DMF (200 ml). The mixture was stirred at 80° C. for 4 hours before the solvent was distilled off and the residue dissolved in ether and washed five times with water, and the dried (MgSO4) solution evaporated. Yield: 5.37 g (92%), m.p. 67° C. (Pet. ether/ether). The product (17.8 mmol) was dissolved in CH2Cl2 (100 ml) and SO2Cl2 (17.8 mmol) in CH2Cl2 (25 ml) was added with stirring at 5° C. for 30 minutes. The mixture was stirred for 15 minutes before cyclohexene (19.3 mmol) in CH2Cl2 (25 ml) was added. The mixture was evaporated and the residue washed with hexane and dried. The product was used in the Example 28 without further purification. 1H NMR (CDCl3,δ): 5.50 (s, --CH2 --), 7.34 (Ph), 8.33 (CHO).

Provenance & Evidence