Dimethylformamide → (+/-)-N,N-dimethyl-2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoropropionamide

HRID 973321Notes

Reaction equation

HRID 973321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][O:13][C:14](C(F)(F)F)([C:18]([F:21])([F:20])[F:19])[C:15](O)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30][N:31](C)[CH:32]=O>>[CH3:30][N:31]([CH3:32])[C:15](=[O:16])[CH:14]([O:13][CH2:12][C:11]1[CH:26]=[CH:27][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 133842612-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid

Product 1

HCID 13384300(+/-)-N,N-dimethyl-2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoropropionamide

Conditions

Temperature
100 °C

Procedure

A solution of 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionic acid (2.06 g.) in dimethylformamide (10 ml.) is added dropwise at 0° C. under argon to a stirred suspension of sodium hydride (216 mg. of a 60% dispersion in oil from which the oil has been washed with light petroleum) in dimethylformamide (15 ml.). The mixture is heated at 100° C. for 18 hours, cooled, and evaporated in vacuo. The residue is mixed with water and the solid obtained (1.8 g.) is washed with water and dried, then chromatographed in toluene on a column of silica (60 g.). The column is washed with toluene (900 ml.) until no more material is eluted, and then with ether. The ether is evaporated and the solid (0.4 g.) is crystallised from light petroleum to give (±)-N,N-dimethyl-2-[4-(4-chlorophenyl)-benzyloxy]-3,3,3-trifluoropropionamide, m.p. 103°-107° C. (212 mg.).

Workup

  1. washof a 60% dispersion in oil from which the oil has been washed with light petroleum) in dimethylformamide (15 ml.)
  2. temperaturecooled
  3. customevaporated in vacuo
  4. additionThe residue is mixed with water
  5. customthe solid obtained (1.8 g.)
  6. washis washed with water
  7. customdried
  8. customchromatographed in toluene on a column of silica (60 g.)
  9. washThe column is washed with toluene (900 ml.) until no more material
  10. washis eluted
  11. customThe ether is evaporated
  12. customthe solid (0.4 g.) is crystallised from light petroleum

Sources & evidence

ORD record
ord-71766b76988b40bd821fb3bc1bfef571
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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