Dimethylformamide → HCID 66726142, compound

HRID 1042092Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13](F)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+].[CH3:33]N(C)C=O>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:30][C:27]2[CH:25]=[CH:24][C:23]([S:26][CH3:33])=[CH:22][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 78114-Methylbenzenethiol

HCID 11430Potassium Carbonate

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 66726142HCID 66726142, compoundYield 93%

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(benzyloxy)-4-fluoro-1-nitrobenzene (16.8 g), 4-methylthiophenol (10.0 g), potassium carbonate (14.1 g), and N,N-dimethylformamide (150 mL) was stirred at 80° C. for 2 hr. The reaction solution was concentrated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained solid was washed with diethyl ether to give the title compound (23.2 g, yield 93%) as a pale-yellow solid. The pale-yellow solid was recrystallized from ethanol to give pale-yellow crystals.

Workup

concentrationThe reaction solution was concentrated under reduced pressure, water
additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed successively with water and saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
washThe obtained solid was washed with diethyl ether

Sources & evidence

ORD record: ord-4da5a91143cb48f8b209b2ecb6b1c580
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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