Dimethylformamide → HCID 14500631, compound

HRID 1761584Notes

Reaction equation

HRID 1761584 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)([O-])=O.CI.[C:21](OCC)(=O)C.C[N:28](C)[CH:29]=[O:30]>>[CH3:21][N:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[CH2:9][C:8]1[CH:16]=[CH:17][CH:18]=[C:6]([NH:3][C:29]([NH2:28])=[O:30])[CH:7]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide3×HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14500627HCID 14500627, compound

Product 1

HCID 14500631HCID 14500631, compoundYield 90%

Conditions

Temperature
0 °C

Procedure

50% Sodium hydride 2.15 g (89 mmol) was suspended, under nitrogen atmosphere, in 100 ml of anhydrous dimethylformamide. A solution of 10 g (46 mmol) of 2-(3'-nitrobenzoyl)pyrrole in 50 ml of anhydrous dimethylformamide was added thereto, and the resulting mixture stirred for 1 hour, cooled to 0° C. and then treated dropwise with a solution of 8.6 ml (130 mmol) of methyl iodide in 30 ml of dry dimethylformamide. The reaction mixture was stirred for an additional hour at 0° C. and thereafter poured into 500 ml of ethyl acetate, the extract was washed with water (5×250 ml), dried and evaporated in vacuo. The residue was crystallized from methylene chloride-hexane, to produce 9.6 g (90%) of the title compound, 1-methyl-2-(3'-nitrobenzoyl)pyrrole. M.P. 115°-117° C. (methylene chloride-methanol)

Workup

  1. stirringThe reaction mixture was stirred for an additional hour at 0° C.
  2. washthe extract was washed with water (5×250 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-6d56005f39624cfe915b048d6c9f902d
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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