Dimethylformamide → HCID 66726142, compound

HRID 1188870Notes

Reaction equation

HRID 1188870 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

5

Reactant 4

HCID 6228DimethylformamideHCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 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 mixture was concentrated under reduced pressure, water was added, and the mixture was subjected to extraction 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 melting point 81-82° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-4647cbb7deb94875a0523f9b27e719ea
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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