1,3-Dichloroacetone → 4-(Chloromethyl)-N,N-dimethyl-1,3-thiazol-2-amine

HRID 742135Notes

Reaction equation

HRID 742135 reaction equation
[CH3:1][N:2]([CH3:6])[C:3]([NH2:5])=[S:4].[O-]S([O-])(=O)=O.[Mg+2].[Cl:13][CH2:14][C:15]([CH2:17]Cl)=O>CC(C)=O>[Cl:13][CH2:14][C:15]1[N:5]=[C:3]([N:2]([CH3:6])[CH3:1])[S:4][CH:17]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 30341921,1-Dimethyl-2-thiourea

Product 1

HCID 152908844-(Chloromethyl)-N,N-dimethyl-1,3-thiazol-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 15 g (144 mmol) of N,N-dimethylthiourea and excess MgSO4 in 350 ml of acetone was heated to reflux and treated dropwise with a solution of 18.3 g (144 mmol) of 1,3-dichloroacetone in 35 ml of acetone. The resulting mixture was heated at reflux for 1.5 h, allowed to cool, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography using 20% ethyl acetate in hexane to provide 14.0 g (70%) of the desired compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 1.5 h
  5. temperatureto cool
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2a229e95a86f4afa94ae5bb3dd52c895
Source dataset
uspto-grants-1996_09
Patent number
US05552558

Reaction notes

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