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

HRID 1029857Notes

Reaction equation

HRID 1029857 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12]([CH2:14]Cl)=O.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[Cl:10][CH2:11][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][CH:14]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 683563Thiobenzamide

Product 1

HCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleYield 86%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of thiobenzamide (13.7 g, 0.10 mol), 1,3-dichloroacetone (12.7 g, 0.10 mol), sodium bicarbonate (8.4 g, 0.10 mol) and dichloroethane (200 mL) is refluxed for 6 hours. The reaction mixture is cooled to 23° C. and the solid by-products are removed by filtration. The filtrate is concentrated under reduced pressure to give the crude product (19.0 g). This material is recrystallized from hexane and the title product is obtained as a light yellow solid (18.2 g) in 86.0% yield, m.p. 44°-48° C.

Workup

  1. temperatureis refluxed for 6 hours
  2. customthe solid by-products are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customto give the crude product (19.0 g)
  5. customThis material is recrystallized from hexane

Sources & evidence

ORD record
ord-9f87e05ec35542a69d220b33b438730a
Source dataset
uspto-grants-1992_04
Patent number
US05103014

Reaction notes

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