1,3-Dichloroacetone → HCID 23371811, compound

HRID 2221681Notes

Reaction equation

HRID 2221681 reaction equation
[C:1]([O:9][CH2:10][C:11]([NH2:13])=[S:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:14][CH2:15][C:16](=O)[CH2:17]Cl>C(O)C>[C:1]([O:9][CH2:10][C:11]1[S:12][CH:17]=[C:16]([CH2:15][Cl:14])[N:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 110743142-Benzoyloxyethanethioamide

Product 1

HCID 23371811HCID 23371811, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-2-thioxoethyl benzoate (7.6 g), 1,3-dichloro-2-propanone (7.6 g) and ethanol (100 mL) was heated under reflux for 4 hrs. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to give (4-chloromethyl-1,3-thiazol-2-yl)methyl benzoate as a brown oil (7.3 g, yield 45%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hrs
  3. customThe solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washeluted with ethyl acetate-hexane (1:5

Sources & evidence

ORD record
ord-d158a8b12e054c7f9b79b30d7911d3e2
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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