Iodoacetamide → HCID 19105303, compound

HRID 1197886Notes

Reaction equation

HRID 1197886 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][NH2:17].I[CH2:19][C:20]([NH2:22])=[O:21].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][NH:17][CH2:19][C:20]([NH2:22])=[O:21]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 516892Sodium BicarbonateHCID 19105314HCID 19105314, compound

Product 1

HCID 19105303HCID 19105303, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel was charged with 5 g (18.4 mmole) of [(2-chlorophenyl)-4-fluorophenyl]methylamine hydrochloride, 3.4 g (18.4 mmole) of iodoacetamide, 3.2 g (3.8 mmole) of sodium bicarbonate and 150 ml of absolute ethanol. The resulting suspension was brought to reflux and held at reflux for 42 hours. Solvent was evaporated under reduced pressure and the residue was dissolved in water. The aqueous phase was extracted with dichloromethane, and then the organic phase was dried over potassium bicarbonate and evaporated under reduced pressure. The brown oil was solidified in a mixture of ethyl acetate and pentane, and then crystallized twice in a mixture of ethyl acetate and pentane.

Workup

  1. temperatureto reflux
  2. temperatureat reflux for 42 hours
  3. customSolvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialthe organic phase was dried over potassium bicarbonate
  7. customevaporated under reduced pressure
  8. additionThe brown oil was solidified in a mixture of ethyl acetate and pentane
  9. customcrystallized twice in a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-0c61cbe8703746c8949d9ba1b43c5e58
Source dataset
uspto-grants-1994_01
Patent number
US05278191

Reaction notes

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