1,3-Dichloroacetone → 2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

HRID 1020239Notes

Reaction equation

HRID 1020239 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Cl:5][CH2:6][C:7]([CH2:9]Cl)=O>CC(C)=O>[ClH:5].[NH2:1][C:2]1[S:3][CH:9]=[C:7]([CH2:6][Cl:5])[N:4]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 2723790Thiourea

Product 1

HCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)Yield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of thiourea (15.0 g, 197.1 mmol) in acetone (750 ml) was added dropwise over three hours to a stirred solution of 1,3-dichloroacetone (24.9 g, 199.8 mmol) in acetone (120 ml). After complete addition, stirring was continued for 18 hours at ambient temperature. The precipitate was collected by filtration and washed with cold acetone. The white solid was dried under vacuum, yield: 90% (32.8 g, 177.2 mmol).

Workup

  1. additionAfter complete addition
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with cold acetone
  4. customThe white solid was dried under vacuum, yield: 90% (32.8 g, 177.2 mmol)

Sources & evidence

ORD record
ord-124223ac4d674513a97e8ae21526fe80
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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