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

HRID 854698Notes

Reaction equation

HRID 854698 reaction equation
[F:1][S:2]([F:17])([F:16])([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.[Cl:18][CH:19](Cl)[C:20](=O)[CH3:21]>C1(C)C=CC=CC=1>[Cl:18][CH2:19][C:20]1[N:13]=[C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([S:2]([F:14])([F:15])([F:16])([F:17])[F:1])=[CH:8][CH:7]=2)[O:12][CH:21]=1

Participants

4

Reactant 2

HCID 105671,1-DichloroacetoneHCID 865985163-(4-Pentafluorosulfanyl-phenyl)-acrylamide

Product 1

HCID 865985174-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.10 g (15.0 mmol) 3-(4-Pentafluorosulfanyl-phenyl)-acrylamide, 2.37 g (18.7 mmol) dichloro acetone and 25.0 ml toluene were kept at reflux temperature for 12 h with continuous removal of water by use of a Dean-Stark trap. The reaction mixture was evaporated and purified by chromatography on silica gel (eluent: heptane/ethyl acetate 5:1). All fractions containing the product were evaporated and the residue stirred with 10 ml isohexane, the crystallized material isolated by filtration dried. Yield: 4.40 g (85%) 4-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 12 h
  2. customwith continuous removal of water by use of a Dean-Stark trap
  3. customThe reaction mixture was evaporated
  4. custompurified by chromatography on silica gel (eluent: heptane/ethyl acetate 5:1)
  5. additionAll fractions containing the product
  6. customwere evaporated
  7. customthe crystallized material isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-7337d9033ddb44269296248e3490b31c
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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