Water → HCID 15480133, compound

HRID 1872777Notes

Reaction equation

HRID 1872777 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:11]C(=O)C(F)(F)F.O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO>[NH2:11][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[N:8][C:7]=2[C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15480132HCID 15480132, compound

Product 1

HCID 15480133HCID 15480133, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-methyl-5-trifluoroacetamidobenzoxazole (3.45 g, 14.13 mmol) in a 20% mixture of water in methanol (20 mL) is treated with anhydrous potassium carbonate (7.80 g, 56.52 mmol). A reflux condenser is attached and the mixture is heated to 90° C. with an oil bath for five hours. The mixture is cooled to room temperature and distributed between ethyl acetate (100 mL) and water (100 mL). The ethyl acetate layer is dried over magnesium sulfate and concentrated under reduced pressure to yield a black residue. This material is purified by chromatography (silica gel, 50% ethyl acetate/hexanes) to afford 2.30 g of 5-amino-4-methylbenzoxazole as an off-white solid.

Workup

  1. customA reflux condenser is attached
  2. temperatureThe mixture is cooled to room temperature
  3. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield a black residue
  6. customThis material is purified by chromatography (silica gel, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fc6bf8f1e7954ba2bdb21eff917f6cdb
Source dataset
uspto-grants-2000_08
Patent number
US06110952

Reaction notes

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