2-Propanesulfonyl chloride → HCID 15604499, compound

HRID 1591817Notes

Reaction equation

HRID 1591817 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.[CH:16]([S:19](Cl)(=[O:21])=[O:20])([CH3:18])[CH3:17]>O>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:19]([CH:16]([CH3:18])[CH3:17])(=[O:21])=[O:20])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

4

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 160504305-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 15604499HCID 15604499, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5-(4-Aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.27 g, 1.37 mmol) was dissolved in isopropyl sulfonyl chloride (0.50 mL, 2.8 mmol) and heated to 70° C. for 6 hours. The mixture was cooled and diluted with water and extracted with ethyl acetate. The organics were combined, washed with water, brine, dried over MgSO4, and concentrated. Flash chromatography (0%-100% ethyl acetate in hexane) afforded N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)phenyl]propane-2-sulfonamide (0.009 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7acc297cceee450cbcca1ef5b3a59d25
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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