1,1-Dichloroacetone → 4-Chloromethyl-2-[2-(4-fluoro-2-trifluoromethyl-phenyl)-vinyl]-oxazole

HRID 1271429Notes

Reaction equation

HRID 1271429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH2:12])=[O:11])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[Cl:17][CH:18](Cl)[C:19](=O)[CH3:20]>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]1[N:12]=[C:10]([CH:9]=[CH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[C:13]([F:14])([F:15])[F:16])[O:11][CH:20]=1

Participants

4

Reactant 2

HCID 105671,1-DichloroacetoneHCID 694870153-(4-Fluoro-2-trifluoromethyl-phenyl)-acrylamide

Product 1

HCID 694876114-Chloromethyl-2-[2-(4-fluoro-2-trifluoromethyl-phenyl)-vinyl]-oxazoleYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(4-Fluoro-2-trifluoromethyl-phenyl)-acrylamide (1.0 g, 4.29 mmol), dichloro acetone (2.18 g, 17.15 mmol) and toluene (10 ml) were kept at reflux temperature for 16 h with continuous removal of water by use of a Dean-Stark trap. After removal of solvents in vacuo, the residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 2:1) yielding 0.93 g (71%) 4-chloromethyl-2-[2-(4-fluoro-2-trifluoromethyl-phenyl)-vinyl]-oxazole as tan solid.

Workup

  1. temperatureat reflux temperature for 16 h
  2. customwith continuous removal of water by use of a Dean-Stark trap
  3. customAfter removal of solvents in vacuo
  4. customthe residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-6a24a7b1d9424372b505de0aef295adf
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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