m-Tolyl isocyanate → 1-(1-Methylpyrrolidin-2-ylidene)-3-(m-tolyl)urea
Reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[C:8]1([CH3:17])[CH:13]=[CH:12][CH:11]=[C:10]([N:14]=[C:15]=[O:16])[CH:9]=1>>[CH3:17][C:8]1[CH:9]=[C:10]([NH:14][C:15]([N:1]=[C:2]2[CH2:6][CH2:5][CH2:4][N:3]2[CH3:7])=[O:16])[CH:11]=[CH:12][CH:13]=1Participants
3
Procedure
Conversion of the hydrochloride salt of 2-imino-1-methylpyrrolidine (6.73 g.; 0.05 mole) to the free base (4.9 g. assuming 100% conversion) is carried out in the usual manner. After drying over K2CO3, the benzene layer is stirred, and 6.66 g. (0.05 mole) of m-tolylisocyanate is added (solid forms). The reaction mixture is stirred at room temperature overnight. The solid is collected, m.p. = 148°-149° C. The benzene filtrate, after removal of solvent, yields a further crop of solid material, m.p. 137°-142° C. Recrystallizations of the combined solids from acetone gives the pure product, 1-m-methylphenyl-3-(1-methyl-2-pyrrolidylidene)urea, m.p. = 149°-151° C.
Workup
- dry with materialAfter drying over K2CO3
- stirringThe reaction mixture is stirred at room temperature overnight