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

HRID 1456320Notes

Reaction equation

HRID 1456320 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 dichlormethane (1 l) and ether (1l). 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 dichlormethane (1 l) and ether (1l)
  6. concentrationThe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-9bf909261f994b4faf3c1db2e5e27d2f
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

Loading…