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

HRID 1939778Notes

Reaction equation

HRID 1939778 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-de5537a9120d478ea8da29217b9ed7b7
Source dataset
uspto-grants-1997_12
Patent number
US05696270

Reaction notes

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