Chloroacetamide → N~2~-(2-Methoxy-5-nitrophenyl)glycinamide

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[Ca+2].Cl[CH2:19][C:20]([NH2:22])=[O:21]>>[C:20]([CH2:19][NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12])(=[O:21])[NH2:22]

Participants

Reactant 3

HCID 6580Chloroacetamide

HCID 74472-Methoxy-5-nitroaniline

HCID 10112Calcium Carbonate

Product 1

HCID 20558418N~2~-(2-Methoxy-5-nitrophenyl)glycinamide

Procedure

In 2.7 liters of hydroalcoholic solution (2/3 alcohol, 1/3 water), one adds 2.1 mols (353 g) of 2-amino-4-nitro anisole, 2.1 mols (210 g) of calcium carbonate and 4.2 mols (393 g) of chloroacetamide. The mixture is brought to reflux for 64 hours and then drained while boiling. The precipitate which contains the expected product mixed with mineral salts is agitated in 1 liter of water at a temperature of 80° C. Hydrochloric acid is added in a quantity sufficient to destroy calcium carbonate. The expected product is drained, washed two times in boiling water, and recrystallized in acetic acid. After vacuum drying the product melts at 224° C.