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

HRID 1939137Notes

Reaction equation

HRID 1939137 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-93973a8818874f8095b4de61c6cffc46
Source dataset
uspto-grants-1997_12
Patent number
US05696001

Reaction notes

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