Chloroacetamide → N~2~-(4-Nitrophenyl)glycinamide

HRID 1391392Notes

Reaction equation

HRID 1391392 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Ca+2].Cl[CH2:17][C:18]([NH2:20])=[O:19]>O.C(O)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:17][C:18]([NH2:20])=[O:19])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 74754-NitroanilineHCID 10112Calcium Carbonate

Product 1

HCID 23104345N~2~-(4-Nitrophenyl)glycinamideYield 58%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of p-nitroaniline (55.2 g, 0.4 mol), calcium carbonate (80 g) and chloroacetamide (149.6 g, 1.6 mol) in 350 ml of water/ethanol (1/1) was refluxed for 42 hours. The resulting mixture was filtered while hot and allowed to cool, and the crystals were filtered off by suction, reslurried in water and then washed with absolute ethanol. After drying, 87.9 g of crude product were obtained. After two recrystallizations from acetonitrile, 45.3 g of pure product were obtained (melting point=178° C.).

Workup

  1. temperaturewas refluxed for 42 hours
  2. filtrationThe resulting mixture was filtered while hot and
  3. temperatureto cool
  4. filtrationthe crystals were filtered off by suction
  5. washwashed with absolute ethanol
  6. customAfter drying
  7. custom87.9 g of crude product were obtained
  8. customAfter two recrystallizations from acetonitrile

Sources & evidence

ORD record
ord-16c0fd29e0ed49c7ae84da016654edbe
Source dataset
uspto-grants-2008_03
Patent number
US07338536B2

Reaction notes

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