Water → N-[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]methanesulfonamide

HRID 1591819Notes

Reaction equation

HRID 1591819 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>N1C=CC=CC=1.C(OCC)(=O)C>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 160504305-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051002N-[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]methanesulfonamideYield 66.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.5 g, 2.3 mmol) was dissolved in pyridine (5 mL), methane sulfonyl chloride (0.16 mL, 2.1 mmol) was added, the mixture was stirred for 4 hours, and then water was added. The mixture diluted with ethyl acetate and the mixture was washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. Flash chromatography (5%-50% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)phenyl]methanesulfonamide (0.382 g).

Workup

  1. washthe mixture was washed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2dc41e7dc2e41398973b76a6a40a3df
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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