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

HRID 1435607Notes

Reaction equation

HRID 1435607 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[NH2:7][C:8]([NH2:10])=[S:9]>CC(C)=O>[ClH:1].[Cl:1][CH2:2][C:3]1[N:7]=[C:8]([NH2:10])[S:9][CH:5]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 2723790Thiourea

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1,3-dichloroacetone (25.4 g, 200 mmol) in acetone (100 mL) was stirred while a solution of thiourea (15.2 g, 200 mmol) in acetone (500 mL) was dropped in at a fairly rapid rate. A clear oil began to separate when the addition was about one quarter complete. The mixture stood over night during which time the oil solidified to a mass of white crystals. After decantation of the acetone, the solid was stirred with EtOH (200 mL). Insoluble material was filtered off and to the solution was petroleumether added. The product separated as an oil which solidified (18 g, 49%): MS (Ionspray, [M+H]+) m/z 148. Anal. Calcd. (found) for C4H5ClN2S.1 HCl: C, 26.0 (26.0)%; H, 3.3 (3.2)%; N, 15.1 (15.1)%.

Workup

  1. additionwas dropped in at a fairly rapid rate
  2. customto separate when
  3. additionthe addition
  4. waitThe mixture stood over night during which time
  5. filtrationInsoluble material was filtered off and to the solution
  6. additionwas petroleumether added
  7. customThe product separated as an oil which

Sources & evidence

ORD record
ord-68cdf78e0ee148f09ee765ce31da10cc
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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