1,1-Dichloroacetone → 4-Chloromethyl-2-[2-(3-trifluoromethoxy-phenyl)-vinyl]-oxazole

HRID 1271432Notes

Reaction equation

HRID 1271432 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([NH2:14])=[O:13])[CH:7]=[CH:8][CH:9]=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:14]=[C:12]([CH:11]=[CH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:15])([F:16])[F:1])[CH:5]=2)[O:13][CH:20]=1

Participants

4

Reactant 2

HCID 105671,1-DichloroacetoneHCID 694896963-(3-Trifluoromethoxy-phenyl)-acrylamide

Product 1

HCID 694901734-Chloromethyl-2-[2-(3-trifluoromethoxy-phenyl)-vinyl]-oxazoleYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(3-Trifluoromethoxy-phenyl)-acrylamide (0.99 g, 4.27 mmol), dichloro acetone (1.90 g, 14.95 mmol) and toluene (8 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 0.76 g (71%) 4-chloromethyl-2-[2-(3-trifluoromethoxy-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-44638753b63944a5b5e05314df6faf6d
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

Loading…