Dimethylformamide → N-(4-(5-Cyano-1-ethyl-1H-pyrrol-2-yl)phenyl)ethanesulfonamide

HRID 1591839Notes

Reaction equation

HRID 1591839 reaction equation
[C:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH3:20][C:21](C)([O-])C.[K+].C(I)C.CN(C)C=O>O1CCCC1>[C:1]([C:3]1[N:7]([CH2:20][CH3:21])[C:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 16051191N-[4-(5-Cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 16051192N-(4-(5-Cyano-1-ethyl-1H-pyrrol-2-yl)phenyl)ethanesulfonamideYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[4-(5-cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamide (0.160 g, 0.58 mmol) was dissolved in tetrahydrofuran (10 mL). Potassium tert-butoxide (1.25 mL of a 1 M solution, 1.25 mmol) was dropwise added and the mixture stirred 15 minutes. Ethyl iodide (0.046 mL, 0.58 mmol) was dropwise added, followed by dimethyl formamide (5 mL) and the mixture stirred for 4 hours. The mixture was then partitioned between saturated ammonium chloride and ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 7:3) to afford the title compound (0.020 g, 11%).

Workup

  1. stirringthe mixture stirred for 4 hours
  2. customThe mixture was then partitioned between saturated ammonium chloride and ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 7:3)

Sources & evidence

ORD record
ord-d52bfe79270f4b6bbb96a594325b8dc6
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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