p-Toluenesulfonic acid → Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate

HRID 2362055Notes

Reaction equation

HRID 2362055 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]2[O:19][C:18]3[C:9](=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=[CH:16][CH:17]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59625786Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate

Product 1

HCID 59626027Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate 9dd (7.4 mmol, 1.2 g crude) and 1.3 g (7.5 mmol) of p-toluenesulfonic acid was refluxed in 10 mL of xylene overnight. After cooling saturated NaHCO3 was added and the resulting mixture was extracted with EtOAc. The organic solvent was evaporated to give 1.1 g (55%) of methyl 2-(4-fluorophenyl)benzo[d]oxazole-4-carboxylate, 9ee. MS m/z (M+H+) 272.0.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with EtOAc
  3. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-0749e945be6c494a9e9b2ee4d60bd388
Source dataset
uspto-grants-2014_04
Patent number
US08691805B2

Reaction notes

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