Water → HCID 53650486, compound

HRID 1646230Notes

Reaction equation

HRID 1646230 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([CH:19]=[CH:20][CH2:21]Cl)=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].O>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:21][CH:20]=[CH:19][C:18]2[CH:23]=[CH:24][C:15]([O:14][CH2:13][O:12][CH3:11])=[C:16]([N+:25]([O-:27])=[O:26])[CH:17]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 53823294HCID 53823294, compound

Product 1

HCID 53650486HCID 53650486, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a current of argon, a solution having 251 mg of sodium hydride suspended in 10 ml of tetrahydrofuran and 906 mg of p-chlorothiophenol added thereto as kept cooled with ice were stirred for 30 minutes and the produced mixture and a solution of 1.62 g of 4-methoxymethoxy-3-nitrocinnamyl chloride in 5 ml tetrahydrofuran added thereto were stirred at normal room temperature for 14 hours. The resultant reaction mixture was combined with water and extracted from ethyl acetate. The consequently separated organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The residue from drying was concentrated under a vacuum. The concentrate was subjected to silica gel column chromatography. From the hexane-ethyl acetate (5:1 V/V) eluate, 1.77 g of 5-[3-(4-chlorophenylthio)-1-propenyl]-2-methoxymethoxy nitrobenzene was obtained in the form of a colorless oily substance. The yield was 77%.

Workup

  1. temperatureas kept cooled with ice
  2. stirringthereto were stirred at normal room temperature for 14 hours
  3. customThe resultant reaction mixture
  4. extractionextracted from ethyl acetate
  5. washThe consequently separated organic layer was washed with saturated saline solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe residue from drying
  8. concentrationwas concentrated under a vacuum

Sources & evidence

ORD record
ord-2e78fa2dc7154cccbb9547c43819dab1
Source dataset
uspto-grants-1993_01
Patent number
US05179105

Reaction notes

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