4-Bromothiobenzamide → 2-(4-Bromophenyl)thiazol-5-ylacetic acid ethyl ester

HRID 1701942Notes

Reaction equation

HRID 1701942 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Br[CH:12]([CH:19]=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C:12]1[S:7][C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)=[N:8][CH:19]=1)[CH3:18]

Participants

4

Reactant 2

HCID 15492894-BromothiobenzamideHCID 15576269Ethyl 3-bromo-4-oxobutanoate

Product 1

HCID 541433512-(4-Bromophenyl)thiazol-5-ylacetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromothiobenzamide (2.16 g., 0.01 mole) and ethyl 3-bromo-4-oxobutyrate (3.2 g., 0.015 mole) in ethanol (50 ml.) is heated at reflux for 6 hours. On cooling and partial evaporation there is obtained 2-(4-bromophenyl)thiazol-5-ylacetic acid ethyl ester. Reaction of this product with ammonia according to the procedure of Example 3 gives 2-(4-bromophenyl)thiazol-5-ylacetamide, which on reaction with diethyl oxalate and base in dimethylformamide, according to the general procedure of Example 6, affords the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. temperatureOn cooling
  4. custompartial evaporation there

Sources & evidence

ORD record
ord-08f603bc20f14c959b7a135c66d27614
Source dataset
uspto-grants-1983_04
Patent number
US04379791

Reaction notes

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