Water → 4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole

HRID 2214972Notes

Reaction equation

HRID 2214972 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O.O.[OH-].[Na+]>C(O)(C)C>[Cl:11][CH2:12][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[S:7][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 107931,3-DichloroacetoneHCID 14798Sodium HydroxideHCID 27348264-Chlorothiobenzamide

Product 1

HCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
20 °C

Procedure

171.65 g (1.0 mol) of 4-chlorothiobenzamide are dissolved in 550 ml of isopropyl alcohol and 133.3 g (1.05 mol) of 1,3-dichloroacetone are added at a temperature of a maximum of 30° C. over a period of 3hours. The mixture is subsequently stirred at 40° C. for 5.5 hours and at 20° C. for 10 hours. In order to complete the reaction the mixture is then heated to 55° C. for 7.5 hours. The product is isolated by cooling to 10° C. and adding 950 ml of water. The pH value is adjusted to 4 to 5 using sodium hydroxide solution and the product is filtered off with suction.

Workup

  1. customthe reaction the mixture
  2. temperatureis then heated to 55° C. for 7.5 hours
  3. customThe product is isolated
  4. temperatureby cooling to 10° C.
  5. filtrationthe product is filtered off with suction

Sources & evidence

ORD record
ord-1d5a9db3ed2b4df5bfaec7da1a4ff889
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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