(2-methylanilino)thiourea

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 27.2 g. (0.15 moles) of 1-(o-tolyl)-3-thiosemicarbazide, 31 g. (0.15 moles) of 2-bromoethylamine hydrobromide, and 800 ml. of isopropanol are heated at reflux temperature for 16 hours. The reaction mixture is cooled to room temperature and filtered. The solid material is washed with hot water and the aqueous solution is treated with saturated sodium bicarbonate solution. The solid material which separates is filtered, washed with water, and recrystallized with methanol affording 13 g. of 2-(o-tolylhydrazino)-2-thiazoline, m.p. 126°-127° C. A mixture of 27.2 g at reflux temperature for 16 hours filtered The solid material is washed with hot water the aqueous solution is treated with saturated sodium bicarbonate solution The solid material which separates is filtered washed with water recrystallized with methanol affording 13 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 15.9 g. (0.1 moles) of o-tolylhydrazine hydrochloride, 15.2 g. (0.2 moles) of ammonium thiocyanate, 300 ml. of ethanol and 30 ml. of water are heated at reflux temperature for 24 hours, the solvent is removed by distillation at atmospheric pressure, and sufficient water added to cause precipitation. The aqueous suspension is filtered and the solid residue recrystallized from aqueous ethanol affording 15 g. (85%) of 1-(o-tolyl)-3-thiosemicarbazide, m.p. 158°-160° C. A mixture of 15.9 g at reflux temperature for 24 hours the solvent is removed by distillation at atmospheric pressure, and sufficient water added precipitation The aqueous suspension is filtered the solid residue recrystallized from aqueous ethanol affording 15 g