Thiophenol → HCID 10783431, compound

HRID 2260681Notes

Reaction equation

[H-].[Na+].Br[CH2:4][C:5]1([CH3:20])[CH2:9][C:8]2[C:10]([CH3:19])=[C:11]([NH:16][CH:17]=[O:18])[C:12]([CH3:15])=[C:13]([CH3:14])[C:7]=2[O:6]1.[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH:17]([NH:16][C:11]1[C:12]([CH3:15])=[C:13]([CH3:14])[C:7]2[O:6][C:5]([CH3:20])([CH2:4][S:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:9][C:8]=2[C:10]=1[CH3:19])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (60% purity, 1.0 g, 21.1 mmol) was added to a solution of 2-bromomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (6.0 g, 19.2 mmol) and thiophenol in dimethylformamide (50 ml) and the mixture was stirred at 80° C. for 1 hour under an argon atmosphere. After the reaction mixture was cooled, the product was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1) and then the purified product was recrystallized from ethanol-isopropyl ether to obtain the desired compound (5.54 g, yield: 83.3% yield), m.p. 130°-131° C.

Workup

temperatureAfter the reaction mixture was cooled
extractionthe product was extracted with ethyl acetate
washThe extract was washed with water
customdried
distillationthe solvent was distilled off
customThe residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1)
customthe purified product was recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record: ord-415aa5ee9c1440a392042e423593bc2b
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478844

Reaction notes

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