Methane → HCID 86738002, compound

HRID 1577569Notes

Reaction equation

HRID 1577569 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[C:7]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([N+:22]([O-])=O)[C:5]1=[S:25](=[O:27])=[O:26].C>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH:4]1[CH:9]=[C:8]([N:10]2[CH:11]=[CH:12][CH:13]=[CH:14]2)[C:7]([S:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([NH2:22])[C:5]1=[S:25](=[O:27])=[O:26]

Participants

5

Reactant 2

HCID 297MethaneHCID 86738000HCID 86738000, compound

Product 1

HCID 86738002HCID 86738002, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

20 g of 3-nitro-4-phenylthio-5-pyrrol-1-yl-sulfonylbenzoic acid methyl ester in 1 liter of ethyl acetate are hydrogenated in the presence of 2 g of palladium on active charcoal, initially at room temperature and then at 40°-50° C. After filtering off the catalyst and concentrating the filtrate under reduced pressure, the residue is chromatographed over a silica gel column, using methylene chloride. The fractions containing the desired product are freed from solvent and the residue is recrystallized from methanol. 3-Amino-4-phenylthio-5-pyrrol-1-yl-sulfonylbenzoic acid methyl ester of melting point 118°-119° C. is obtained.

Workup

  1. customat 40°-50° C
  2. filtrationAfter filtering off the catalyst
  3. concentrationconcentrating the filtrate under reduced pressure
  4. customthe residue is chromatographed over a silica gel column
  5. additionThe fractions containing the desired product
  6. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-069e44b014fe48c1aff59eac95fd127f
Source dataset
uspto-grants-1981_09
Patent number
US04288449

Reaction notes

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