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

HRID 1591818Notes

Reaction equation

HRID 1591818 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.[CH2:16]([S:18](Cl)(=[O:20])=[O:19])[CH3:17].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:18]([CH2:16][CH3:17])(=[O:20])=[O:19])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

6

Reactant 3

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 160504305-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16051001N-[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]ethanesulfonamideYield 80.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (1.3 g, 6 mmol) was dissolved in pyridine (10 mL), ethane sulfonyl chloride (0.54 mL, 5.7 mmol) was added, the mixture was stirred for 4 hours, and then water was added. The mixture was diluted with ethyl acetate and 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]ethanesulfonamide (1.33 g).

Workup

  1. washwashed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9f52457683404a74b1b3a2fb8b96c44e
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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