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

HRID 1659805Notes

Reaction equation

HRID 1659805 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

4

Reactant 3

HCID 6580ChloroacetamideHCID 74472-Methoxy-5-nitroanilineHCID 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.

Workup

  1. temperatureto reflux for 64 hours

Sources & evidence

ORD record
ord-2fe7379ce74c4b06be22f8fc3b4d22df
Source dataset
uspto-grants-1981_12
Patent number
US04305717

Reaction notes

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