2-Amino-4-methoxyphenol → 5-Methoxy-2-(3-trifluoromethylphenyl)-benzoxazole

HRID 22699Notes

Reaction equation

HRID 22699 reaction equation
Cl.[CH2:2]([O:4][C:5](=[NH:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[CH3:3].NC1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20]C=1O>C1COCC1>[CH3:25][O:24][C:22]1[CH:23]=[CH:3][C:2]2[O:4][C:5]([C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:15])[F:14])[CH:7]=3)=[N:16][C:20]=2[CH:21]=1

Participants

4

Reactant 2

HCID 14191082-Amino-4-methoxyphenolHCID 2730239Ethyl 3-(trifluoromethyl)benzene-1-carboximidate hydrochloride

Product 1

HCID 121354125-Methoxy-2-(3-trifluoromethylphenyl)-benzoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 13 and compound 12 (850 mg, 6.13 mmol) in THF (10 mL) was heated to reflux and allowed to stir overnight. The reaction mixture was allowed to cool and the THF evaporated (in vacuo). The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over MgSO4 and treated with activated carbon Norit A. The mixture was filtered through Celite 521, and evaporated (in vacuo) and the residue was purified using column chromatography (20% Ethyl acetate/hexanes) to afford compound 10 as a light yellow solid.

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. customthe THF evaporated (in vacuo)
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. additiontreated with activated carbon Norit A
  8. filtrationThe mixture was filtered through Celite 521
  9. customevaporated (in vacuo)
  10. customthe residue was purified

Sources & evidence

ORD record
ord-222adf13858b4f44a1c49bfc04e45445
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Reaction notes

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