Chloroacetamide → HCID 19105302, compound

HRID 1197884Notes

Reaction equation

HRID 1197884 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][NH2:16])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl[CH2:18][C:19]([NH2:21])=[O:20].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][NH:16][CH2:18][C:19]([NH2:21])=[O:20])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 191053273′,4′-Dimethyl[1,1′-biphenyl]-2-methanamine

Product 1

HCID 19105302HCID 19105302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel was charged with 11.5 g (54.5 mmole) of [(3,4-dimethylphenyl)phenyl]methylamine dissolved in 200 ml of absolute ethanol. A mixture of 5.05 g (54 mmole) of chloracetamide and 4.62 g (55 mmole) of sodium bicarbonate was added to the reaction vessel and the solution was brought to refulux and held at reflux for 42 hours. Solvent was evaporated under reduced pressure and the residue was diluted with water. The aqueous phase was extracted with dichloromethane and the organic solution dried over potassium carbonate. After evaporation of solvent under reduced pressure, the solid residue was crystallized in ethyl acetate.

Workup

  1. additionwas added to the reaction vessel
  2. temperatureat reflux for 42 hours
  3. customSolvent was evaporated under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialthe organic solution dried over potassium carbonate
  7. customAfter evaporation of solvent under reduced pressure
  8. customthe solid residue was crystallized in ethyl acetate

Sources & evidence

ORD record
ord-fe0e229bb5bb49278dab95c582792070
Source dataset
uspto-grants-1994_01
Patent number
US05278191

Reaction notes

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