2-Amino-5-methoxybenzene-1,3-diol → 2-(2,5-Difluorophenyl)-6-methoxy-1,3-benzoxazol-4-ol

HRID 2056627Notes

Reaction equation

I.[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10](SC)=[NH:11].N[C:15]1[C:20]([OH:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=1[OH:24]>C(O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]1[O:21][C:20]2[C:15](=[C:16]([OH:24])[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=2)[N:11]=1

Participants

Conditions

Temperature: 78 °C

Procedure

2.8 g (9.02 mmol; 1 equivalent) of methyl 2,5-difluorobenzene carbimidothioate hydroiodide in solution in 20 ml of ethanol is added to a solution of 1.4 g (9.02 mmol) of 2-amino-5-methoxybenzene-1,3-diol in 80 ml of ethanol. The reaction mixture is maintained under stirring at 78° C. for 5 hours then the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 98:2) and 860 mg (34% yield) of 2-(2,5-difluorophenyl)-6-methoxy-1,3-benzoxazol-4-ol is obtained.

Workup

temperatureThe reaction mixture is maintained
customthe solvent is evaporated off under reduced pressure
customThe residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 98:2)

Sources & evidence

ORD record: ord-26a5b2433e074f29872a285fdfa2d37e
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335674B2

Reaction notes

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