Dimethylformamide → 3-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-amino-6-trifluoromethyluracil

HRID 366316

Reaction equation

C[N:2](C)C=O.[Cl:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:16][CH3:17])[O:15][C:11]=2[C:10]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[NH:20][C:19]2=[O:29])=[C:9]([F:30])[CH:8]=1.[N+](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:16][CH3:17])[O:15][C:11]=2[C:10]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[N:20]([NH2:2])[C:19]2=[O:29])=[C:9]([F:30])[CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

80 ml of N,N-dimethylformamide was added to 3.4 g (9.0 mmol) of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil, 2.7 g (14 mmol) of 2,4-dinitrophenoxyamine and 5.0 g (36 mmol) of potassium carbonate, followed by stirring at 60 to 70° C. for 1 hour. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.0 g (yield: 58%) of the desired product as white crystals. Melting point: 145-147° C.

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate
washThe organic layer was washed sequentially with water
dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-6b136cb4a742421583c4eabc5cf768e4
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Linked notes

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