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

HRID 1271421Notes

Reaction equation

HRID 1271421 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([NH2:16])=[O:15])=[CH:8][CH:7]=1)([F:4])[F:3].[Cl:17][CH:18](Cl)[C:19](=O)[CH3:20]>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]1[N:16]=[C:14]([CH:13]=[CH:12][C:9]2[CH:8]=[CH:7][C:6]([S:5][C:2]([F:4])([F:3])[F:1])=[CH:11][CH:10]=2)[O:15][CH:20]=1

Participants

4

Reactant 2

HCID 105671,1-DichloroacetoneHCID 691120573-(4-Trifluoromethylsulfanyl-phenyl)-acrylamide

Product 1

HCID 691129774-Chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.45 g (18.0 mmol) 3-(4-Trifluoromethylsulfanyl-phenyl)-acrylamide, 2.79 g (22.0 mmol) dichloro acetone and 50.0 ml toluene were kept at reflux temperature for 30 h with continuous removal of water by use of a Dean-Stark trap. The reaction mixture was cooled for 30 min. in an ice bath and the precipitated amide (1.2 g) was removed by filtration and discarded. After removal of solvents in vacuo, the residue (5.92 g) was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 1:1). All fractions containing the product were concentrated to a volume of 10 ml, n-heptane added and the crystallized material isolated by filtration, washed with cold heptane and dried. 2.02 g (35%) 4-Chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 30 h
  2. customwith continuous removal of water by use of a Dean-Stark trap
  3. temperatureThe reaction mixture was cooled for 30 min. in an ice bath
  4. customthe precipitated amide (1.2 g) was removed by filtration
  5. customAfter removal of solvents in vacuo
  6. customthe residue (5.92 g) was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 1:1)
  7. additionAll fractions containing the product
  8. concentrationwere concentrated to a volume of 10 ml, n-heptane
  9. additionadded
  10. customthe crystallized material isolated by filtration
  11. washwashed with cold heptane
  12. customdried

Sources & evidence

ORD record
ord-641723665ade45ccbd8441b3fce5f981
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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