Butyl bromide → HCID 14500642, compound

HRID 1761591Notes

Reaction equation

HRID 1761591 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].Br[CH2:20][CH2:21][CH2:22][CH3:23].C(OCC)(=O)C>CN(C)C=O>[CH2:20]([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)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 8002Butyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14500627HCID 14500627, compound

Product 1

HCID 14500642HCID 14500642, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4 G (160 mmol) of 50% sodium hydride were suspended, under nitrogen atmosphere, in 250 ml of anhydrous dimethylformamide. A solution of 15 g (69 mmol) of 2-(3-nitrobenzoyl)pyrrole, prepared, for example, as described in Preparation 3A, in 50 ml of anhydrous dimethylformamide was added thereto, in a dropwise fashion and under stirring, maintaining the temperature at 20°-25° C. The resulting mixture was stirred for 2 additional hours and then a solution of 18 ml (170 mmol) of 1-bromobutane in 50 ml of dry dimethylformamide was added. The reaction mixture was stirred at room temperature for 18 hours further and then poured into 2000 ml of ethyl acetate. The organic extract was washed with water (5×500 ml), dried and evaporated in vacuo. The residue was purified by column chromatography on 1 Kg of silica gel, using hexane-acetone (90:10) as eluant, thus obtaining 18 g (95%) of 1-butyl-2 -(3'-nitrobenzoyl)pyrrole, the title compound, as an oil.

Workup

  1. additionwas added
  2. temperaturemaintaining the temperature at 20°-25° C
  3. stirringThe resulting mixture was stirred for 2 additional hours
  4. stirringThe reaction mixture was stirred at room temperature for 18 hours further
  5. extractionThe organic extract
  6. washwas washed with water (5×500 ml)
  7. customdried
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on 1 Kg of silica gel

Sources & evidence

ORD record
ord-20ba53d96af149dcbf859ae7265209a2
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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