Thiophenol → Ethyl 2-phenylthio-4-methyl-5-thiazolecarboxylate

HRID 1678873Notes

Reaction equation

HRID 1678873 reaction equation
Br[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:13]1([S:19][C:2]2[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 20364661Ethyl 2-phenylthio-4-methyl-5-thiazolecarboxylateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of ethyl 2-bromo-4-methyl-5-thiazolecarboxylate (22 g), thiophenol (10.75 g) and potassium carbonate powder (24.3 g) in dimethylformamide (100 ml) is stirred for 4 hours at 80° C. The reaction mixture is treated in the same manner as in Example 1 to give ethyl 2-phenylthio-4-methyl-5-thiazolecarboxylate (24.2 g) boiling at 160°-161° C at 1 mmHg.

Workup

  1. additionThe reaction mixture is treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-9e5e8529e0a04289a38b9b4ade8e8c60
Source dataset
uspto-grants-1978_03
Patent number
US04077968

Reaction notes

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