1,1-Dichloroacetone → HCID 69293306, compound

HRID 750983Notes

Reaction equation

HRID 750983 reaction equation
[CH3:1][S:2][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:14][CH:15](Cl)[C:16](=O)[CH3:17]>C1(C)C(C)=CC=CC=1>[Cl:14][CH2:15][C:16]1[N:13]=[C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=2)[O:12][CH:17]=1

Participants

4

Reactant 2

HCID 105671,1-DichloroacetoneHCID 67012321HCID 67012321, compound

Product 1

HCID 69293306HCID 69293306, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.00 g (10.3 mmol) 3-(4-methylsulfanyl-phenyl)-acrylamide, 2.63 g (22.0 mmol) dichloro acetone and 60.0 ml xylene were kept at reflux temperature for 3 h with continuous removal of water by use of a Dean-Stark trap (a water separator used in chemical reactions). After removal of solvents in vacuo, the residue was partitioned between ethyl acetate and water. The organic extracts were dried and the solvent was distilled off. The remaining residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 1:3). Yield: 1.50 g (55%) 4-Chloromethyl-2-[2-(4-methylsulfanyl-phenyl)-vinyl]-oxazole as a light yellow solid melting at 126-128° C.

Workup

  1. temperatureat reflux temperature for 3 h
  2. customwith continuous removal of water by use of a Dean-Stark trap (a water
  3. customAfter removal of solvents in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic extracts were dried
  6. distillationthe solvent was distilled off
  7. customThe remaining residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 1:3)

Sources & evidence

ORD record
ord-4a6d9196f7cc42c6b170a3372f10157a
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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