Chloroacetamide → N~2~-(Diphenylmethyl)glycinamide

Reaction equation

[C:1]1([CH:7]([NH2:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:16][C:17]([NH2:19])=[O:18].C(=O)(O)[O-].[Na+]>C(O)C>[C:1]1([CH:7]([NH:14][CH2:16][C:17]([NH2:19])=[O:18])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Procedure

A reaction vessel was charged with 18.3 g (100 mmole) of diphenylmethylamine dissolved in 250 ml of ethanol. Then a mixture of 9.35 g (100 mmole) of chloroacetamide and 8.4 g (100 mmole) of sodium bicarbonate was added and the suspension was brought to reflux and held at reflux for 3 days. Solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was washed with water, dried over potassium carbonate and solvent was evaporated. The resulting solid crystallized from a mixture of benzene and cyclohexane.