Iodoethane → HCID 14500632, compound

HRID 1761587Notes

Reaction equation

HRID 1761587 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[C:9]([C:11]1[NH:12][CH:13]=[CH:14][CH:15]=1)=[O:10])([O-:5])=[O:4].[CH2:19](I)[CH3:20].C(OCC)(=O)C>CN(C)C=O>[CH2:19]([N:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9](=[O:10])[C:8]1[CH:16]=[CH:17][CH:18]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14500627HCID 14500627, compound

Product 1

HCID 14500632HCID 14500632, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3.2 g (130 mmol) of 50% sodium hydride were suspended, under nitrogen atmosphere, in 100 ml of anhydrous dimethylformamide. A solution of 12 g (55 mmol) of 2-(3'-nitrobenzoyl)pyrrole, prepared, for example, as described in Preparation 3A, in 50 ml of dimethylformamide was added thereto, at room temperature and under stirring. The resulting mixture was stirred for an additional hour and then treated dropwise with a solution of 11.2 ml (70 mmol) of ethyl iodide in 30 ml of dry dimethylformamide. The reaction mixture was stirred for an additional hour and then poured into 500 ml of ethyl acetate. The organic extract was washed with water (5×250 ml), dried and evaporated in vacuo. Crystallization of the residue from acetone-hexane afforded 10.55 g (78%) of 1-ethyl-2-(3'-nitrobenzoyl)pyrrole, the title compound.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred for an additional hour
  3. stirringThe reaction mixture was stirred for an additional hour
  4. extractionThe organic extract
  5. washwas washed with water (5×250 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customCrystallization of the residue from acetone-hexane

Sources & evidence

ORD record
ord-62f48d75e82d42ebbc18c853db606a59
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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