Benzamide → 2-Phenyl-5-ethyl-oxazole-4-carboxylic acid

HRID 2300589Notes

Reaction equation

HRID 2300589 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH2:19][CH3:20])[C:12](=O)[C:13]([O:15]CC)=[O:14]>C1(C)C=CC=CC=1>[CH2:19]([C:11]1[O:8][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][C:12]=1[C:13]([OH:15])=[O:14])[CH3:20]

Participants

4

Reactant 2

HCID 2331BenzamideHCID 147403343-BroMo-2-oxo-pentanoic acid ethyl ester

Product 1

HCID 150939472-Phenyl-5-ethyl-oxazole-4-carboxylic acidYield 9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Intermediate 1E was prepared (as described below for the preparation of intermediate 2B) from 4.08 g of benzamide, 5.0 g of ethyl 3-bromo-2-oxo-pentanoate, and 10 mL of toluene. Solids were collected and washed with cold water after cooling of the NaOH solution. Heating these solids with citric acid as described followed by cooling and isolation of the resulting solids gave 410 mg (9% yield) of the title compound; 1H NMR (CDCl3, 300 MHz) δ8.06-8.03 (m, 2H), 7.49-7.43 (m, 3H), 3.14 (q, 2H, J=8.0), 1.34 (t, 3H, J=8.0); low resolution MS (ES+)m/e 217.8 (MH+).

Workup

  1. customIntermediate 1E was prepared (
  2. customSolids were collected
  3. washwashed with cold water
  4. temperatureafter cooling of the NaOH solution
  5. temperatureHeating these solids with citric acid
  6. temperatureby cooling

Sources & evidence

ORD record
ord-aee0ead58b5146d4bed786a4a7964a42
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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