Dichloromethane → 2-[4-(3-Chloropropoxy)phenyl]-1,3-thiazole

HRID 1710778Notes

Reaction equation

HRID 1710778 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[CH:16](OCC)[CH2:17]CCl.ClCCl>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:14][CH:16]=[CH:17][N:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 553014301,3-Dichloro-1-ethoxy-propaneHCID 594574624-(3-Chloropropoxy)benzenecarbothioamide

Product 1

HCID 542513932-[4-(3-Chloropropoxy)phenyl]-1,3-thiazoleYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4-(3-chloropropoxy)benzenecarbothioamide ax71 (0.3 g, 1 eq, 1.31 mmol) in ethyl alcohol (5 ml) is treated with 1,3-dichloro-1-ethoxy-propane (0.4 ml, 2.7 eq, 3.6 mmol) and the mixture is stirred at 110° C. during 4 h. The mixture is then poured into dichloromethane (10 ml) and is washed with water. The organic phase is dried over magnesium sulfate and concentrated. Purification by chromatography over silicagel (eluent: dichloromethane) affords 120 mg of 2-[4-(3-chloropropoxy)phenyl]-1,3-thiazole i88.

Workup

  1. washis washed with water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by chromatography over silicagel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-1a190a4eb9f544a9920a3b63f89ab882
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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