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

HRID 1852593Notes

Reaction equation

HRID 1852593 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-a15130bd8be54ef3bd26b9db468d8965
Source dataset
uspto-grants-2015_02
Patent number
US08962607B2

Reaction notes

Loading…