1,3-Dichloroacetone → 4-(Chloromethyl)-2-isopropyl-1,3-thiazole

HRID 2221601Notes

Reaction equation

HRID 2221601 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=[S:5])[NH2:4].[Cl:7][CH2:8][C:9](=O)[CH2:10]Cl>C(O)C>[Cl:7][CH2:8][C:9]1[N:4]=[C:3]([CH:2]([CH3:6])[CH3:1])[S:5][CH:10]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 109095072-Methylpropanethioamide

Product 1

HCID 27631934-(Chloromethyl)-2-isopropyl-1,3-thiazoleYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methylpropanethioamide (5.20 g), 1,3-dichloro-2-propanone (7.03 g) and ethanol (100 mL) was heated under reflux for 2 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4-chloromethyl-2-isopropyl-1,3-thiazole as a colorless oil (6.33 g, yield 72%) from a fraction eluted with ethyl acetate-hexane (1:20, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4bf50cc30d74d1c9a79bc098aa65cef
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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