1,3-Dichloroacetone → 4-(Chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-thiazole

HRID 1710747Notes

Reaction equation

HRID 1710747 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8][CH:7]=1.[Cl:15][CH2:16][C:17]([CH2:19]Cl)=O>C(#N)CC>[Cl:15][CH2:16][C:17]1[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:7][CH:8]=2)[S:14][CH:19]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 594574624-(3-Chloropropoxy)benzenecarbothioamide

Product 1

HCID 594574714-(Chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-thiazoleYield 91%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
100 °C

Procedure

4-(3-chloropropoxy)benzenecarbothioamide ax71 (0.9 g, 4 mmole, 1 eq) is dissolved in propionitrile (20 ml) and 1,3-dichloroacetone (0.6 g, 4.7 mmole, 1.17 eq) is added. The mixture is refluxed 1 h at 100° C. then concentrated to dryness. The crude material is taken up in dichloromethane, washed with water and dried over magnesium sulfate. The residue is triturated in diisopropylether and filtered off to give 1.1 g of 4-(chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-thiazole ax72 as a white solid.

Workup

  1. concentrationthen concentrated to dryness
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe residue is triturated in diisopropylether
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-52416b7dc7ca4bc28ed783bcf8b564ee
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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