Potassium Carbonate → 2-Oxazol-2-yl-benzoic acid methyl ester

HRID 419112Notes

Reaction equation

HRID 419112 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](Cl)=[O:11].[NH:14]1[CH:18]=[CH:17]N=N1.C(=O)([O-])[O-].[K+].[K+]>C1S(=O)(=O)CCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:11][CH:17]=[CH:18][N:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11159939Methyl 2-(carbonochloridoyl)benzoateHCID 178418936HCID 178418936, compound

Product 1

HCID 579422612-Oxazol-2-yl-benzoic acid methyl esterYield 18.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-Chlorocarbonyl-benzoic acid methyl ester (1.3 gram, 6.56 mmol), 1H-triazole (0.42 ml, 7.22 mmol) and potassium carbonate (2.78 g, 20 mmol) in 12 ml of tetramethylene sulfone was heated at 140° C. for half an hour. The mixture was cooled, diluted with ethyl acetate, washed with water 5 times, and dried. After concentration the crude was purified by flash column (50% ethyl acetate in hexane) to afford 250 mg of 2-Oxazol-2-yl-benzoic acid methyl ester as a light yellow liquid. MS: (M+H)/z=204.1.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water 5 times
  3. customdried
  4. concentrationAfter concentration the crude
  5. customwas purified by flash column (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-786aef03e474405aa365fb1d307fee1b
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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