Formaldehyde → benzyl 2-(N-methyleneamino)-2-methylpropanoate
Reaction equation
[CH2:1]=O.[NH2:3][C:4]([CH3:16])([CH3:15])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]>C(OCC)C>[CH2:1]=[N:3][C:4]([CH3:16])([CH3:15])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
37% Aqueous formaldehyde solution (17.3 g) was added over 10 minutes to a stirred solution of benzyl 2-amino-2-methylpropanoate (28.0 g) in diethyl ether at ambient temperature. The two phase mixture was stirred for 21/2 hours then diluted with diethyl ether and washed with brine. The ethereal solution was dried (magnesium sulphate) and solvent evaporated under reduced pressure to give benzyl 2-(N-methyleneamino)-2-methylpropanoate (29.4 g) in equilibrium with its trimer 1,3,5-tri(1-benzyloxycarbonyl-1-methylethyl)hexahydrotriazine as a colourless oil, IR (liquid film) 2980(m), 1725(vs), 1250(m), 1135(vs).