Dimethylformamide → HCID 14500608, compound

HRID 1761597Notes

Reaction equation

HRID 1761597 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)[C:9]([C:11]1[NH:12][C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=1)=O)([O-])=O.Br[CH2:23][CH2:24][CH3:25].C[N:27](C)[CH:28]=[O:29]>>[CH2:23]([N:12]1[C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=[C:11]1[CH2:9][C:8]1[CH:19]=[CH:20][CH:21]=[C:6]([NH:3][C:28]([NH2:27])=[O:29])[CH:7]=1)[CH2:24][CH3:25]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 14500603HCID 14500603, compound

Product 1

HCID 14500608HCID 14500608, compoundYield 98%

Procedure

2.5 g (100 mmol) of 50% sodium hydride were suspended, under nitrogen atmosphere, in 150 ml of anhydrous dimethylformamide. A solution of 11.5 g (44 mmol) of 2-(3'-nitrobenzoyl)-5-propylpyrrole in 50 ml of anhydrous dimethylformamide was added thereto, in a dropwise fashion and under stirring. The resulting mixture was stirred at room temperature for an additional hour and then 10 ml (110 mmol) of 1-bromopropane was added. The reaction mixture was stirred at room temperature for 48 hours, and thereafter poured into 500 ml of ice-ethyl acetate. The organic phase was separated. The aqueous phase was extracted with more ethyl acetate (2×500 ml), and the combined orgainc extracts were washed with water (5×300 ml), dried and evaporated in vacuo. Purification of the residue by column chromatography on 500 g of silica gel, using hexane-acetone (90:10) as eluant provided 13.9 g (98%) of the title compound, 1,5-dipropyl-2-(3'-nitrobenzoyl)pyrrole, as an oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for an additional hour
  2. stirringThe reaction mixture was stirred at room temperature for 48 hours
  3. customThe organic phase was separated
  4. extractionThe aqueous phase was extracted with more ethyl acetate (2×500 ml)
  5. washthe combined orgainc extracts were washed with water (5×300 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customPurification of the residue by column chromatography on 500 g of silica gel

Sources & evidence

ORD record
ord-20790327d66c4ac1b443bd6bbf31623d
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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