Water → HCID 69220008, compound

HRID 2056626Notes

Reaction equation

FC(F)(F)[C:3](OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=[O:4].[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[C:30]1[O:31][C:32]2[C:38](N)=[CH:37][C:36]([O:40]C)=[CH:35][C:33]=2[N:34]=1.[OH2:42]>C(#N)C.O>[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[C:30]1[O:42][C:35]2[C:36](=[O:40])[CH:37]=[C:38]([O:4][CH3:3])[C:32](=[O:31])[C:33]=2[N:34]=1

Participants

Conditions

Temperature: -5 °C

Procedure

7 g (16.2 mmol; 2.2 equivalents) of bis(trifluoroacetoxy)iodobenzene dissolved in 130 ml of an acetonitrile/water mixture 4/1 is added dropwise to a solution of 2.04 g (7.38 mmol) of 2-(2,5-difluorophenyl)-5-methoxy-1,3-benzoxazol-7-amine in 75 ml of an acetonitrile/water mixture 4:1 at −5° C. After stirring for 1 hour at −5° C., 150 ml of water is added to the reaction medium and the product formed is extracted with twice 300 ml of dichloromethane. The organic phases are combined and dried over sodium sulphate, then the solvents are evaporated off under reduced pressure. The residue is then purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 98:2) and 200 mg (10% yield) of 2-(2,5-difluorophenyl)-5-methoxy-1,3-benzoxazole-4,7-dione is obtained in the form of a yellow powder.

Workup

customthe product formed
extractionis extracted with twice 300 ml of dichloromethane
dry with materialdried over sodium sulphate
customthe solvents are evaporated off under reduced pressure
customThe residue is then purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 98:2)

Sources & evidence

ORD record: ord-b8d0dcfad62a4cfe83949d478fc76903
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335674B2

Reaction notes

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