Sodium Bicarbonate → 5-Bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamide

HRID 389710Notes

Reaction equation

HRID 389710 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]#[N:16].C(=O)(O)[O-:18].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[O:6][C:5]([C:7]2[C:8]([F:14])=[CH:9][CH:10]=[CH:11][C:12]=2[F:13])=[N:4][C:3]=1[C:15]([NH2:16])=[O:18]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 595875125-Bromo-2-(2,6-difluorophenyl)oxazole-4-carbonitrile

Product 1

HCID 595875995-Bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-bromo-2-(2,6-difluorophenyl)oxazole-4-carbonitrile (0.010 g, 0.04 mmol) in concentrated H2SO4 (0.4 mL) was stirred at room temperature for 4 hours. The reaction was neutralised with saturated sodium bicarbonate solution and extracted with EtOAc. The organic phase was dried over MgSO4 and the solvent removed in vacuo to afford 5-bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.010 g, 0.03 mmol, 94%) as a white solid. 1H NMR (CDCl3) δ 5.79 (1H, br. s), 6.95 (1H, br. s), 7.07 (2H, t), 7.49 (1H, m). LCMS (1) Rt: 1.59 min; m/z (ES+) 303/305.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-034fdbcd8b614a9c8b474d931a24f719
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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