Water → N-(1-ethyl-5-formyl-1H-pyrrol-3-yl)-N-methylthiophene-2-sulfonamide

HRID 453576Notes

Reaction equation

HRID 453576 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([N:8]([CH3:17])[S:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)(=[O:11])=[O:10])[CH:5]=[C:4]1[C:18](OCC)=[O:19])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:3]1[C:4]([CH:18]=[O:19])=[CH:5][C:6]([N:8]([CH3:17])[S:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:11])=[CH:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59411397ethyl 1-ethyl-4-[methyl(2-thienylsulfonyl)amino]-1H-pyrrole-2-carboxylate

Product 1

HCID 59411382N-(1-ethyl-5-formyl-1H-pyrrol-3-yl)-N-methylthiophene-2-sulfonamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-ethyl-4-[methyl(2-thienylsulfonyl)amino]-1H-pyrrole-2-carboxylate (11.9 g) in tetrahydrofuran (200 mL) was slowly added lithium aluminum hydride (1.46 g) in small portions. The reaction mixture was stirred at room temperature for 1 hr, and water (1.5 mL), 15% aqueous sodium hydroxide solution (1.5 mL) and water (4.5 mL) were successively added to the reaction mixture under ice-cooling. The reaction mixture was stirred for 1 hr, the insoluble material was filtered off, and the filtrate was concentrated. To a solution of the residue in tetrahydrofuran (200 mL) was added manganese dioxide (12 g), and the mixture was stirred at room temperature overnight. The manganese dioxide was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give N-(1-ethyl-5-formyl-1H-pyrrol-3-yl)-N-methylthiophene-2-sulfonamide (9.5 g, yield 91%) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 1 hr
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated
  5. additionTo a solution of the residue in tetrahydrofuran (200 mL) was added manganese dioxide (12 g)
  6. stirringthe mixture was stirred at room temperature overnight
  7. filtrationThe manganese dioxide was filtered off
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b2e9466ba0e144aab9cbdcae72389a61
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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