1,3-Dichloroacetone → 2-Acetamido-4-chloromethylthiazole

HRID 272738

Reaction equation

HRID 272738 reaction equation
[C:1]([NH:4][C:5]([NH2:7])=[S:6])(=[O:3])[CH3:2].[Cl:8][CH2:9][C:10]([CH2:12]Cl)=O>CC(C)=O.C(OCC)(=O)C>[Cl:8][CH2:9][C:10]1[N:7]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][CH:12]=1

Participants

5

Reactant 2

HCID 107931,3-DichloroacetoneHCID 2723593Acetylthiourea

Product 1

HCID 819632-Acetamido-4-chloromethylthiazole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of acetylthiourea (591 mg, 5 mmol) and 1,3-dichloroacetone (667 mg, 5.25 mmol) in acetone (15 mL) was heated at reflux for 7 hours, cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography to give the title compound. MS (DCI) m/e 191 (M+H)+; 1H NMR (300 MHz, DMSO-d6) 12.21 (s, 1H), 7.22 (s, 1H), 4.70 (s, 2H), 2.13 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-ad2bf5bf99c34722b2d7b275df5bf4b6
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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