Sodium Carbonate → 2-(4'-Trifluoromethylphenyl)-6-hydroxybenzoxazole

HRID 265214Notes

Reaction equation

HRID 265214 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:21]=[CH:20][C:18]([OH:19])=[CH:17][C:16]=1O.C(=O)([O-])[O-].[Na+].[Na+]>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]2[O:8][C:16]3[CH:17]=[C:18]([OH:19])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 4328274-Aminoresorcinol

Product 1

HCID 214669512-(4'-Trifluoromethylphenyl)-6-hydroxybenzoxazole

Procedure

1.5 ml (10 mmol) of 4-trifluoromethylbenzoyl chloride were heated to 190° C. in an oil bath and 1.6 g (10 mmol) of 4-aminoresorcinol were added in portions. After 1 hour the reaction mixture was introduced into 100 ml of 10% strength sodium carbonate solution and heated. The unreacted acid chloride was hydrolyzed during this procedure. The product was then extracted with ethyl acetate and purified by column chromatography (silica gel 60, ethyl acetate or chloroform/glacial acetic acid 9:1).

Workup

  1. temperatureheated
  2. extractionThe product was then extracted with ethyl acetate
  3. custompurified by column chromatography (silica gel 60, ethyl acetate or chloroform/glacial acetic acid 9:1)

Sources & evidence

ORD record
ord-b356f05bc5ba4c558fda3b378cee2c1d
Source dataset
uspto-grants-1997_07
Patent number
US05648229

Reaction notes

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