Sodium hydride → HCID 70922273, compound

HRID 524973Notes

Reaction equation

HRID 524973 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8].[H-].[Na+].C1(C)C=C(C)C=C(C)C=1S(O[NH2:31])(=O)=O>CN(C=O)C>[NH2:31][N:4]1[CH:5]=[CH:6][C:2]([CH3:1])=[C:3]1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 709222793-Methyl-N-o-tolyl-1H-pyrrole-2-carboxamide

Product 1

HCID 70922273HCID 70922273, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-N-o-tolyl-1H-pyrrole-2-carboxamide (1.5 g, 7.00 mmol) was dissolved in 60 mL of DMF. 294 mg (7.35 mmol) of sodium hydride (60 wt % dispersion in mineral oil) were added and the reaction mixture was stirred at room temperature for 1 hour. Then O-(mesitylsulfonyl)hydroxylamine (1.658 g, 7.70 mmol) was added and the reaction mixture was stirred for 30 minutes. The solvent was evaporated to dryness and the crude product was purified by flash chromatography (0 to 50% heptane/AcOEt) to give 1.17 g (73% yield) of the title compound as a yellow solid.

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. customThe solvent was evaporated to dryness
  3. customthe crude product was purified by flash chromatography (0 to 50% heptane/AcOEt)

Sources & evidence

ORD record
ord-c53a1c66857344e48c889215ec5a9ef5
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

Loading…