HCID 10755187, compound → HCID 10824576, compound

HRID 1353014Notes

Reaction equation

HRID 1353014 reaction equation
[CH3:1][C:2]1[N:3]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C:4]([CH3:7])=[CH:5][CH:6]=1>[Ni].CO>[CH3:1][C:2]1[N:3]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 10755187HCID 10755187, compound

Product 1

HCID 10824576HCID 10824576, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]nitrobenzene (Step 1) (7.3 g, 26 mmol) and Raney Nickel (0.7 g) in 70 mL of methanol was hydrogenated in a Parr apparatus at a pressure of 50 psi. After 3 hours, the catalyst was filtered and the filtrate was concentrated to give 4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]benzenamine (6.4 g) as a pale yellow solid: mp (DSC): 110–111° C. Anal. Calc'd. for C12H14N2O2S: C, 57.58; H, 5.64; N, 11.16; S, 12.81. Found: C, 57.44; H, 5.78; N, 11.11; S. 12.30.

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-139e18eba45b4cbbbc0ddd1f841a1d03
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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