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

HRID 744755Notes

Reaction equation

HRID 744755 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-dfecaaca717c4dca96424e3ae4b46e74
Source dataset
uspto-grants-1996_09
Patent number
US05559158

Reaction notes

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