Water → HCID 23289163, compound

HRID 366340Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[C:8]([CH2:12][C:13]#[N:14])=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[C:4]([F:28])[CH:3]=1.[OH2:29]>S(=O)(=O)(O)O>[C:13]([CH2:12][C:8]1[C:7]2[C:2]([Cl:1])=[CH:3][C:4]([F:28])=[C:5]([N:15]3[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]3=[O:27])[C:6]=2[O:10][C:9]=1[CH3:11])(=[O:29])[NH2:14]

Participants

Conditions

Temperature: 60 °C

Procedure

0.50 g (1.2 mmol) of 3-(4-chloro-3-cyanomethyl-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 30 ml of 50% sulfuric acid, followed by stirring at 60° C. for 2 hours. 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 0.39 g (yield: 75%) of the desired product as white crystals. Melting point: 127-129° 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-da518ba120114cdcbd772d0b7e42451a
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

Loading…