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

HRID 892253Notes

Reaction equation

HRID 892253 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][C:14]([NH2:16])=[O:15].[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]1[N:16]=[C:14]([CH:13]=[CH:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=2[F:1])[O:15][CH:21]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 691109983-(2-Fluoro-4-trifluoromethyl-phenyl)-acrylamide

Product 1

HCID 690723654-Chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazoleYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.00 g (17.1 mmol) 3-(2-Fluoro-4-trifluoromethyl-phenyl)-acrylamide, 2.60 g (21.3 mmol) 1,3-dichloroacetone and 40 ml toluene were kept at reflux temperature for 16 h with continuous removal of water by use of a water separator (Dean-Stark trap). After cooling to room temperature, two extractions with 100 ml water were performed, the organic phase was dried over sodium sulphate and the solvent removed in vacuo. Chromatography on silica gel (eluent: n-heptane/ethyl acetate 5:1) gave 1.20 g (23%) 4-chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 16 h
  2. customwith continuous removal of water by use of a water separator (Dean-Stark trap)
  3. extractiontwo extractions with 100 ml water
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-71f2121bc8a74d908ad2b34c678e4d08
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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