Dimethylformamide → HCID 14500626, compound

HRID 1761578Notes

Reaction equation

HRID 1761578 reaction equation
[H-].[Na+].[C:3]([C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)(=O)[CH3:4].[CH3:11][C:12]1[CH:16]=[CH:15][NH:14][C:13]=1[C:17](=O)[CH3:18].Br[CH2:21][CH2:22][CH2:23][CH3:24].C[N:26](C)[CH:27]=[O:28]>C(OCC)(=O)C>[CH2:21]([N:7]1[C:6]([CH2:3][CH3:4])=[CH:10][CH:9]=[C:8]1[CH2:11][C:12]1[CH:13]=[CH:17][CH:18]=[C:15]([NH:14][C:27]([NH2:26])=[O:28])[CH:16]=1)[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 5

HCID 6228Dimethylformamide3×HCID 8002Butyl bromideHCID 140792-AcetylpyrroleHCID 24758Sodium hydrideHCID 44718447HCID 44718447, compound

Product 1

HCID 14500626HCID 14500626, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10.6 g (440 mmol) of 60% sodium hydride were suspended, under nitrogen atmosphere, in 100 ml of anhydrous dimethylformamide and then a solution of 20 g (183 mmol) of 2-acetylpyrrole, prepared, for example, as described in Preparation 1A, in 100 ml of anhydrous dimethylformamide was added thereto, in a dropwise fashion and under stirring, at room temperature. The resulting mixture was stirred for 2 hours further and then treated dropwise with a solution of 25 ml (230 mmol) of 1-bromobutane in 50 ml of dry dimethylformamide. The reaction mixture was kept at room temperature for 18 additional hours, and thereafter poured into 1000 ml of ethyl acetate, washed with water (5×500 ml), dried and evaporated in vacuo, thus obtaining 16.9 g (56%) of the title compound, 1-butyl-2-acetylpyrrole, as an oil.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred for 2 hours further
  3. customwas kept at room temperature for 18 additional hours
  4. washwashed with water (5×500 ml)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0d494b63c4454ac485cb64887090eb6e
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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