Water → 4-Ethylbenzo[d]oxazol-5-amine

HRID 1872785Notes

Reaction equation

HRID 1872785 reaction equation
[CH2:1]([C:3]1[C:8]2[N:9]=[CH:10][O:11][C:7]=2[CH:6]=[CH:5][C:4]=1[NH:12]C(=O)C(F)(F)F)[CH3:2].O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO>[NH2:12][C:4]1[CH:5]=[CH:6][C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 154801414-Ethyl-5-trifluoroacetamidobenzoxazole

Product 1

HCID 154801424-Ethylbenzo[d]oxazol-5-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-ethyl-5-trifluoroacetamidobenzoxazole (14.13 mmol) in a 20% mixture of water in methanol (20 mL) is treated with anhydrous potassium carbonate (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 5-amino-4-ethylbenzoxazole.

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-dd41e73abcee457db3f9e19b0346cdc1
Source dataset
uspto-grants-2000_08
Patent number
US06110952

Reaction notes

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