Chloroacetamide → HCID 19105318, compound

HRID 1197882Notes

Reaction equation

HRID 1197882 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][NH2:15])=[CH:4][CH:3]=1.Cl[CH2:17][C:18]([NH2:20])=[O:19].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][NH:15][CH2:17][C:18]([NH2:20])=[O:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 1393509HCID 1393509, compound

Product 1

HCID 19105318HCID 19105318, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel was charged with 7.62 g (30 mmole) of [(4-chlorophenyl)phenyl]methylamine dissolved in 150 ml of absolute ethanol. A mixture of 2.34 g (25 mmole) of chloracetamide and 5.46 g (5 mmole) of sodium bicarbonate was added to the vessel and the resulting suspension was brought to reflux and held at reflux for 2 days. The solution was then cooled, filtered and evaporated under reduced pressure. The residue was dissolved in water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure. The oily residue was solidified in pentane and crystallized in toluene.

Workup

  1. additionwas added to the vessel
  2. temperatureto reflux
  3. temperatureat reflux for 2 days
  4. temperatureThe solution was then cooled
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in water
  8. extractionextracted with dichloromethane
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. customevaporated under reduced pressure
  11. customcrystallized in toluene

Sources & evidence

ORD record
ord-09c389c422284ee7b73ff93700dcb2c8
Source dataset
uspto-grants-1994_01
Patent number
US05278191

Reaction notes

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