Chloroacetamide → N~2~-(Diphenylmethyl)glycinamide

HRID 1197887Notes

Reaction equation

HRID 1197887 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

5

Reactant 3

HCID 6580ChloroacetamideHCID 7036BenzhydrylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 319782N~2~-(Diphenylmethyl)glycinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. additionwas added
  2. temperatureto reflux
  3. temperatureat reflux for 3 days
  4. customSolvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washThe organic phase was washed with water
  7. dry with materialdried over potassium carbonate and solvent
  8. customwas evaporated
  9. customThe resulting solid crystallized from a mixture of benzene and cyclohexane

Sources & evidence

ORD record
ord-7fe1206630344099a7a079b2e5bad12a
Source dataset
uspto-grants-1994_01
Patent number
US05278191

Reaction notes

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