4-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-nitrobenzene → 4-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-phenylamine

HRID 723560Notes

Reaction equation

HRID 723560 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][C:14]2[CH:29]=[CH:28][C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)=[CH:28][CH:29]=2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 218768834-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-nitrobenzene

Product 1

HCID 691445944-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-phenylamineYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-(4-Methoxyphenyl)sulfonylaminomethylbenzyl]-nitrobenzene (791 mg) was dissolved in ethyl acetate (15 mL) and hydrogenated over 5% palladium on carbon at room temperature. The reaction was allowed to proceed for 6 hours, filtered, and evaporated to dryness. The crude product thus obtained was chromatographed on a short silica column, eluting with hexane/ethyl acetate (1:1), to give 4-[4-(4-methoxyphenyl)sulfonylaminomethylbenzyl]-phenylamine (645 mg, 87%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customThe crude product thus obtained
  4. customwas chromatographed on a short silica column
  5. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d555c74325004831af1de400bd456683
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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