Thiophenol → HCID 86738000, compound

HRID 1577568Notes

Reaction equation

HRID 1577568 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[CH3:11][O:12][C:13](=[O:32])[CH:14]1[CH:19]=[C:18]([N:20]2[CH:24]=[CH:23][CH:22]=[CH:21]2)[C:17](Cl)=[C:16]([N+:26]([O-:28])=[O:27])[C:15]1=[S:29](=[O:31])=[O:30]>C1COCC1>[CH3:11][O:12][C:13](=[O:32])[CH:14]1[CH:19]=[C:18]([N:20]2[CH:24]=[CH:23][CH:22]=[CH:21]2)[C:17]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:16]([N+:26]([O-:28])=[O:27])[C:15]1=[S:29](=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10942334Sodium MethoxideHCID 86738001HCID 86738001, compound

Product 1

HCID 86738000HCID 86738000, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 24.5 ml of thiophenol in 100 ml of anhydrous THF is added to a suspension of 13 g of sodium methylate in 440 ml of absolute THF whilst stirring at room temperature under nitrogen. 72 g of 4-chloro-3-nitro-5-pyrrol-1-yl-sulfonylbenzoic acid methyl ester in 220 ml of absolute THF are then added dropwise and the mixture is stirred at room temperature until the end of the reaction is reached, as ascertained by thin layer chromatography. After removing the solvent on a rotary evaporator, the residue is repeatedly extracted with hexane and then recrystallized from ethyl acetate/methanol. 3-Nitro-4-phenylthio-5-pyrrol-1-yl-sulfonyl-benzoic acid methyl ester of melting point 153°-154° C. is obtained. Yield: 45%.

Workup

  1. stirringthe mixture is stirred at room temperature until the end of the reaction
  2. customAfter removing the solvent
  3. customon a rotary evaporator
  4. extractionthe residue is repeatedly extracted with hexane
  5. customrecrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-dc2b80f07c0049bea5b16f16e365968f
Source dataset
uspto-grants-1981_09
Patent number
US04288449

Reaction notes

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