Phenol → Ethyl 2-phenoxy-5-thiazolecarboxylate

HRID 2398641Notes

Reaction equation

HRID 2398641 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:18]([C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 13106142Ethyl 2-phenoxy-5-thiazolecarboxylateYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 2-bromo-5-thiazolecarboxylate(10 g), phenol (4.38 g) and potassium carbonate powder (11.7 g) are suspended in dimethylformamide (50 ml) and the suspension is stirred for 3 hours at 80° C. The reaction mixture is treated in the same manner as in Example 1 to give ethyl 2-phenoxy-5-thiazolecarboxylate (10.2 g) boiling at 127°-128° C. at 1 mmHg.

Workup

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

Sources & evidence

ORD record
ord-5735cdddb8db458baf5f60070f5733c1
Source dataset
uspto-grants-1977_05
Patent number
US04025528

Reaction notes

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