C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[OH:21].[OH-].[Na+]>CC(C)=O>[OH:21][C:20]1[CH:19]=[C:18]([CH3:22])[CH:17]=[CH:16][C:15]=1[NH:14][C:11]([NH2:12])=[S:10]0.2 mole of benzoyl chloride is added dropwise to a solution of 0.22 mole of ammonium thiocyanate in 100 ml of anhydrous acetone. The mixture is boiled to reflux for 5 minutes after the addition is complete, and a solution of 0.2 mole of 6-amino-m-cresol in 50 ml of anhydrous acetone is then added dropwise so as to maintain gentle refluxing. Stirring and heating are continued for 5 minutes after the addition, the reaction mixture is poured into 1.5 l of ice-cold water, and the crystals obtained are drained and suspended in 300 ml of 10% strength sodium hydroxide solution. The mixture is is brought to boiling for 10 minutes, and the solution is filtered on glass wool and acidified strongly with concentrated hydrochloric acid. The solution is brought back to pH 8 with ammonia solution. The crystals which precipitate on cooling are drained, washed with water and recrystallized in ethanol. (M.p. 175°-7° C.) Yld: 65%.
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