Dimethylformamide → HCID 57667896, compound

HRID 1673354Notes

Reaction equation

HRID 1673354 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([SH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)C=O.Br[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([N+:31]([O-:33])=[O:32])[CH:22]=1>C(OCC)(=O)C>[N+:31]([C:23]1[CH:22]=[C:21]([CH2:20][S:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 19777981HCID 19777981, compound

Product 1

HCID 57667896HCID 57667896, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.01 g of potassium carbonate and 0.39 mL of thiophenol were added to 10 mL of N,N-dimethylformamide solution containing 1.00 g of methyl 4-(bromomethyl)-2-nitrobenzoate at room temperature and stirred at the same temperature for 7 hours. Ethyl acetate was added to the reaction mixture and insoluble were removed by filtration and water was added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=4:1] to obtain 0.70 g of methyl 2-nitro-4-((phenylthio)methyl)benzoate as pale yellow oil.

Workup

  1. custominsoluble were removed by filtration and water
  2. additionwas added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-dbd1b8bbfed3496ebf925e2f2559f996
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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