1,3-Dichloroacetone → HCID 69291784, compound

HRID 750976Notes

Reaction equation

HRID 750976 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14](=[S:16])[NH2:15])=[CH:8][CH:7]=1)([F:4])[F:3].[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O>CC(C)=O>[Cl:17][CH2:18][C:19]1[N:15]=[C:14]([CH:13]=[CH:12][C:9]2[CH:8]=[CH:7][C:6]([S:5][C:2]([F:1])([F:4])[F:3])=[CH:11][CH:10]=2)[S:16][CH:21]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 86070359HCID 86070359, compound

Product 1

HCID 69291784HCID 69291784, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.00 g (7.6 mmol) 3-(4-trifluoromethylsulfanyl-phenyl)-acrylthioamide, 2.90 g (22.8 mmol) 1,3-dichloroacetone and 60 ml acetone were stirred at room temperature for 4 days, then refluxed for 4 h. The product was precipitated by addition of water, isolated and dried, and purified on silica. Elution with ethyl acetate/heptane 1:1 yielded 1.80 g (71%) 4-chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-thiazole as yellow solid, melting at 133-134° C.

Workup

  1. temperaturerefluxed for 4 h
  2. customThe product was precipitated by addition of water
  3. customisolated
  4. customdried
  5. custompurified on silica
  6. washElution with ethyl acetate/heptane 1:1

Sources & evidence

ORD record
ord-2b434449eb4b46a7adc2a8f675695e77
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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