Nitrogen → HCID 20515447, compound

HRID 1902477Notes

Reaction equation

HRID 1902477 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH3:10])[C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].N#N.F[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26]>CN(C)C=O>[CH3:10][N:6]1[C:7]([CH3:9])=[CH:8][C:4]([NH:3][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[C:5]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 20515483HCID 20515483, compound

Product 1

HCID 20515447HCID 20515447, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.0 g (0.2 mole) of commercially available 80% sodium hydride (in paraffin) are added to a solution of 18.2 g (0.1 mole) of ethyl 3-amino-1,5-dimethyl-1H-pyrrole-2-carboxylate in 200 ml of dry dimethylformamide at 0° C. under an inert gas atmosphere (N2). After 1 hour, the evolution of gas has subsided. 28 g (0.2 mole) of 2-fluoronitrobenzene are added dropwise in the course of 30 minutes. After 3 hours, the mixture is allowed to come to room temperature and is poured on to 100 g of ice and extracted several times with ethyl acetate. The combined extracts are washed with water and dried over sodium sulfate. The solvent is stripped off in vacuo. The resulting yellow-orange oil crystallizes completely after a short time. Yield: 22.5 g.

Workup

  1. waitAfter 3 hours
  2. customto come to room temperature
  3. extractionextracted several times with ethyl acetate
  4. washThe combined extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe resulting yellow-orange oil crystallizes completely after a short time

Sources & evidence

ORD record
ord-1e1a47e36ec34fbd9bea1fb2433b5dc0
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Reaction notes

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