1,3-Dichloroacetone → 4-(Chloromethyl)-2-(propan-2-yl)-1,3-thiazole--hydrogen chloride (1/1)

HRID 1081134Notes

Reaction equation

HRID 1081134 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=[S:5])[NH2:4].[Cl:7][CH2:8][C:9]([CH2:11]Cl)=O.[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[ClH:7].[Cl:7][CH2:8][C:9]1[N:4]=[C:3]([CH:2]([CH3:6])[CH3:1])[S:5][CH:11]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 109095072-Methylpropanethioamide

Product 1

HCID 187588464-(Chloromethyl)-2-(propan-2-yl)-1,3-thiazole--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 94.0 g (0.91 mol) of 2-methylpropane-thioamide, 115.7 g (0.91 mol) of 1,3-dichloroacetone, and 109.7 g (0.91 mol) of MgSO4 in 1.6 liters of acetone was heated at reflux for 3.5 h. The resulting mixture was allowed to cool, filtered, and the solvent was removed in vacuo to provide the crude desired compound as a yellow oil. 1H NMR (DMSO-d6) δ1.32 (d, J=7 Hz, 6H), 3.27 (heptet, J=7 Hz, 1H), 4.78 (s, 2H), 7.61 (s, 1H). Mass spectrum: (M+H)+ =176.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6776011dc6704df7a8d9fa44c2729d4f
Source dataset
uspto-grants-1996_12
Patent number
US05583232

Reaction notes

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