1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → N-(2,5-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10](=[N:13][C:14](=O)[CH3:15])SC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N)C[NH2:30]>CCCCCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10]1[NH:30][CH2:15][CH2:14][N:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.8 g (0.01 M) of N-(2,5-dichlorophenyl)-N'-acetyl-S-methylisothiourea and 7.0 g (0.03 M) of ethylenediamine mono-p-toluenesulphonate are boiled with 30 ml of n-amyl alcohol for 5 hours. The reaction solution is washed with 50 ml of a saturated solution of sodium carbonate and 50 ml of water. The amyl alcohol is distilled off under vacuum until a dry residue is obtained which after being recrystallized from ethylacetate gives 1.5 g (65% of the theoretical yield of 2-(2',5'-dichlorophenylamino)-imidazoline (2) with a melting point of 179°-182° C. The hydroiodide salt of the above compound has a melting point of 275°-277° C. According to the U.S. Pat. No. 2,899,426 the melting point of 2-(2',5'-dichlorophenylamino)-imidazoline-(2) hydroiodide is 275.4°-277°.