Iodoacetamide → HCID 19105306, compound

HRID 1197885Notes

Reaction equation

HRID 1197885 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][NH2:15])[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].I[CH2:22][C:23]([NH2:25])=[O:24]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][NH:15][CH2:22][C:23]([NH2:25])=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 516892Sodium BicarbonateHCID 1392233HCID 1392233, compound

Product 1

HCID 19105306HCID 19105306, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel was charged with 8.8 g (40 mmole) of [(3-chlorophenyl)phenyl]methylamine, 4.2 g (50 mmole) of sodium bicarbonate, 7.4 g (40 mmole) of iodoacetamide and 200 ml of absolute ethanol. The resulting suspension was brought to reflux and held at reflux for 18 hours. Solvent was evaporated and the residue was dissolved in dichloromethane. The organic phase was washed with water, dried over potassium carbonate and evaporated. The oil was dissolved in a minimum of ethanol, to which was added a solution of chlorhydric acid in ether. An oil was decanted which crystallized upon stirring. The white solid was then precipitated from ethanol by addition of ether.

Workup

  1. temperatureto reflux
  2. temperatureat reflux for 18 hours
  3. customSolvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe organic phase was washed with water
  6. dry with materialdried over potassium carbonate
  7. customevaporated
  8. dissolutionThe oil was dissolved in a minimum of ethanol, to which
  9. additionwas added a solution of chlorhydric acid in ether
  10. customAn oil was decanted which
  11. customcrystallized
  12. customThe white solid was then precipitated from ethanol by addition of ether

Sources & evidence

ORD record
ord-0fb7b7d360bc4577976b7ac7eb616718
Source dataset
uspto-grants-1994_01
Patent number
US05278191

Reaction notes

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