Potassium Carbonate → Oxazole, 5-[3-fluoro-4-(trifluoromethyl)phenyl]-

HRID 714052Notes

Reaction equation

HRID 714052 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=[O:6].C1(C)C=CC(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:25]=[N:24][CH:23]=2)[CH:7]=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 86699311Oxazole, 5-[3-fluoro-4-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-fluoro-4-(trifluoromethyl)benzaldehyde (1.40 g, 7.07 mmol) and p-toluenesulfonylmethyl isocyanide (1.53 g, 7.68 mmol; TosMIC) in MeOH (100 mL) was treated with potassium carbonate (1.97 g, 14.14 mmol) and the suspension heated to reflux for 14 h. After being cooled to room temperature, the solvent was removed under reduced pressure and the crude product triturated with water at 0° C. (2×25 mL). The slightly orange precipitate was collected by filtration and dried under vacuum (4.46 g, 92%). MS: 232.0 (M+H)+.

Workup

  1. temperaturethe suspension heated
  2. temperatureto reflux for 14 h
  3. customthe solvent was removed under reduced pressure
  4. customthe crude product triturated with water at 0° C. (2×25 mL)
  5. filtrationThe slightly orange precipitate was collected by filtration
  6. customdried under vacuum (4.46 g, 92%)

Sources & evidence

ORD record
ord-6700f5b63f0847f69204989a9b920da9
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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