Dimethyl Sulfate → HCID 178503010, compound

Participants

Reaction Steps

56.6 G (0.5 mole) of caprolactam were fused and 63.1 g (0.5 mole) of dimethyl sulfate were allowed to run into the melt at 70° to 80°C. The mixture was kept at 80° to 90°C for a further 2 hours and cooled, and the viscous melt was taken up in 250 ml of methanol. Reaction with 72 g (0.5 mole) of 3-chlorophenylhydrazine was then carried out in the same manner as indicated in Example 1a, and 99.5 g (57% of theory) of caprolactam-(3-chlorophenylhydrazone) monomethylsulfate were obtained as colorless crystals of melting point 135°C. On concentrating the mother liquors and treating with excess sodium hydroxide solution, 33.3 g (28% of theory) of caprolactam-(3-chlorophenylhydrazone) of boiling point 180°C/0.08 mmHg were obtained. The total yield was 85% of theory.

Provenance & Evidence