Dimethylformamide → 1-(3-methyl-4-nitrobenzyl)-2-(trifluoroacetyl)-1H-pyrrole

HRID 2243259Notes

Reaction equation

HRID 2243259 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].CN(C=O)C.[H-].[Na+].[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[CH2:23]Cl>C(OCC)(=O)C>[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[CH2:23][N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:3](=[O:4])[C:2]([F:1])([F:10])[F:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 137637Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-2-yl)-

Product 1

HCID 592104031-(3-methyl-4-nitrobenzyl)-2-(trifluoroacetyl)-1H-pyrroleYield 90.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(Trifluoroacetyl)-1H-pyrrole (0.97 g) was added to DMF solution (10 ml) of 60% sodium hydride (0.16 g) and the mixture was stirred at room temperature for 30 minutes. 3-Methyl-4-nitrobenzyl chloride (1.0 g) was added thereto and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitrobenzyl)-2-(trifluoroacetyl)-1H-pyrrole (1.53 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. washwashed with water and saturated aqueous solution of sodium chloride
  3. dry with materialAfter drying the organic layer with magnesium sulfate
  4. distillationthe solvent was distilled off under the reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d9ebad4efec4517874fe4a38195b6bc
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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