Triethylamine → HCID 16050901, compound

HRID 1591810Notes

Reaction equation

HRID 1591810 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.C(N(CC)CC)C.[CH2:23]([S:26](Cl)(=[O:28])=[O:27])[CH2:24][CH3:25]>ClCCl.CCOCC.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:26]([CH2:23][CH2:24][CH3:25])(=[O:28])=[O:27])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 160504305-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 16050901HCID 16050901, compoundYield 25.7%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Aminophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (98 mg, 0.5 mmol) was dissolved in dichloromethane (2 mL) and triethylamine (87 μL, 0.6 mmol) was added. Propane sulfonyl chloride (62 μL, 0.55 mmol) was added and the mixture was stirred 16 hours. The mixture was diluted with 50% ether in ethyl acetate and washed with water, saturated NaHCO3, 2N HCl, 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-1-sulfonamide (0.039 g).

Workup

  1. washwashed with water, saturated NaHCO3, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b34b79abdd6c493aa98de6b0fd27323d
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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