Dimethylformamide → Methyl 2-[(dimethylcarbamothioyl)-oxy]-4-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 350 g of methyl 2-hydroxy-4-methoxybenzoate, 648 g of 1,4-diazabicyclo[2.2.2]-octane (DABCO) and 3 L of dimethylformamide was added 712 g of dimethylthiocarbamoyl chloride. The mixture was warmed to 50° C. and held for 7 hours, then allowed to cool overnight. The mixture was poured into 10 L water; the aqueous mixture was extracted with 8 L of benzene-hexane (4:1). The organic solution was washed with 1N HCl, 10% NaOH, and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave 396 g of the title compound, m.p. 95°-105° C. Further extraction of the aqueous mixture gave additional product, 171 g, m.p. 117°-120° C. Recrystallization of a portion of the crude product from methanol gave pure material, m.p. 122°-124° C.

Provenance & Evidence