Dimethylformamide → HCID 57667896, compound

HRID 2191628Notes

Reaction equation

HRID 2191628 reaction equation
CN(C)C=O.Br[CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[N+:18]([C:10]1[CH:9]=[C:8]([CH2:7][S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])([O-:20])=[O:19]

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

To N,N-dimethylformamide 10 mL solution of methyl 4-(bromomethyl)-2-nitrobenzoate 1.0 g, were added potassium carbonate 1.0 g and benzenethiol 0.39 mL at room temperature, and it was stirred at same temperature for 7 hours. Ethyl acetate was added to the reaction mixture, insoluble matter was filtrated, and water was added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=4:1] to give methyl 2-nitro-4-((phenylthio)methyl)benzoate 0.70 g of pale yellow oil.

Workup

  1. filtrationwas filtrated
  2. additionwater was added to it
  3. customThe organic layer was separated
  4. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7c7297f694c14e48969307ab31e8c4ea
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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