Hydrochloric Acid → HCID 178526175, compound

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Reaction Steps

A solution of 15.2 g (0.2 mol) of thiourea in 100 ml of water is introduced into a 1 liter three-necked flask equipped with a magnetic stirrer, a condenser and a dropping funnel, and 28.9 g (0.2 mol) of p-fluorobenzyl chloride are added all at once, at 50°-60° C. The mixture is heated to reflux temperature, boiling is maintained for about 15 minutes and the solution becomes limpid. Thereafter the solution is cooled and a solution of 32 g (0.8 mol) of NaOH in water is added dropwise at about 60° C. The whole is heated under reflux for about 30 minutes, the mixture is cooled and a solution of about 0.28 mol of sodium chloroacetate (obtained by neutralising 26.46 g of chloroacetic acid in 200 ml of water with 23.52 g of sodium bicarbonate) is added dropwise at 60°-70° C. Thereafter the whole is heated under reflux for 30 minutes and then cooled. The mixture is acidified with 3 N HCl and the oil which is obtained is taken up in methylene chloride, this mixture is washed with a dilute sodium bicarbonate solution, filtered over charcoal and acidified once more with 3 N HCl; p-fluorobenzylthioacetic acid is thus precipitated, and is filtered off. After recrystallising from cyclohexane, 33.4 g (yield: 83%) of the said acid are collected. Instantaneous melting point: 68°-69° C.

Provenance & Evidence