Chloroacetamide → HCID 19105313, compound

HRID 1197883Notes

Reaction equation

HRID 1197883 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][NH2:16])=[CH:5][CH:4]=1.Cl[CH2:18][C:19]([NH2:21])=[O:20].C(=O)(O)[O-].[Na+].CCOCC.CCCCC>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([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:7][CH:8]=1

Participants

6

Reactant 4

HCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 1393258HCID 1393258, compoundHCID 21877078Diethylether pentane

Product 1

HCID 19105313HCID 19105313, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel was charged with 800 mg (3.8 mmole) of [(4-methoxyphenyl)phenyl]methylamine dissolved in 30 ml of absolute ethanol together with 340 mg (3.7 mmole) of chloracetamide and 330 mg (4 mmole) of sodium bicarbonate. The suspension was brought to reflux and held at reflux for 3 days. Solvent was evaporated and the residue was dissolved in dichloromethane and water. The organic phase was dried over potasium carbonate and the solvent evaporated under reduced pressure. The oil obtained was solidified by stirring in an ether pentane mixture. The solid was crystallized in cyclohexane with a few drops of ethyl acetate.

Workup

  1. temperatureto reflux
  2. temperatureat reflux for 3 days
  3. customSolvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. dry with materialThe organic phase was dried over potasium carbonate
  6. customthe solvent evaporated under reduced pressure
  7. customThe oil obtained
  8. customThe solid was crystallized in cyclohexane with a few drops of ethyl acetate

Sources & evidence

ORD record
ord-340ab96281714bdf9bbe447ea9e848ef
Source dataset
uspto-grants-1994_01
Patent number
US05278191

Reaction notes

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