Carbon Tetrachloride → N-(4-Benzyloxy-phenyl)-2,2,2-trifluoro-acetimidoyl chloride

HRID 376268Notes

Reaction equation

HRID 376268 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=O)[C:36]([F:39])([F:38])[F:37])=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)(Cl)(Cl)[Cl:42]>>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]([Cl:42])[C:36]([F:39])([F:38])[F:37])=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 21197250N-(4-Benzyloxy-phenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 21197258N-(4-Benzyloxy-phenyl)-2,2,2-trifluoro-acetimidoyl chloride

Procedure

A mixture of resin-supported triphenylphosphine (3 mmol triphenylphosphine/g resin; 58.6 g) and N-(4-benzyloxy-phenyl)-2,2,2-trifluoro-acetamide (20.8 g) in carbon tetrachloride (800 ml) was heated to reflux under nitrogen for 18 h. The mixture was allowed to cool then filtered, washing the resin with dichloromethane (1 l) and ether (1 l). The organics were concentrated in vacuo to give the title compound as a yellow solid (20.7 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 18 h
  3. temperatureto cool
  4. filtrationthen filtered
  5. washwashing the resin with dichloromethane (1 l) and ether (1 l)
  6. concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-ff8f8b36494f484eaaa4c16e11728584
Source dataset
uspto-grants-2000_02
Patent number
US06020346

Reaction notes

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