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

HRID 1941506Notes

Reaction equation

HRID 1941506 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 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 (1l) and ether (1l). The organics were concentrated in vacuo to give the title compound as a yellow solid (20.7 g). T.l.c. (Cyclohexanelethyl acetate (9:1)) Rf 0.81

Workup

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

Sources & evidence

ORD record
ord-5f6274e27f8f4682834b29df24f95f0c
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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