Water → 6-Benzoxazolol, 2-(trifluoromethyl)-

HRID 1271824Notes

Reaction equation

HRID 1271824 reaction equation
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:14][C:11]([F:12])([F:13])[C:10]1[O:15][C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=2[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 18454996N-(2,4-dihydroxyphenyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 184549866-Benzoxazolol, 2-(trifluoromethyl)-Yield 40.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 0.8 gram (0.0036) of N-(2,4-dihydroxyphenyl)-2,2,2-trifluoroacetamide and a catalytic amount of p-toluenesulfonic acid in 50 mL of toluene was heated at reflux during an 18 hour period while the theoretical amount of water by-product was collected in a Dean-Stark trap. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customwas collected in a Dean-Stark trap
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  3. customThe residue was purified with column chromatography on silica gel
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8b1e945ae2243caabc427497c88209b
Source dataset
uspto-grants-2007_04
Patent number
US07208450B2

Reaction notes

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