1-Fluoro-3-nitrobenzene → HCID 19425982, compound

HRID 742336Notes

Reaction equation

HRID 742336 reaction equation
[C:1]([C:4]1[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].[H][H].F[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1>CS(C)=O>[C:1]([C:4]1[C:12]2[N:11]=[CH:10][N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178466152HCID 178466152, compound

Product 1

HCID 19425982HCID 19425982, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Acetylbenzimidazole (4.4 g, 27.5 mmol) was dissolved in dry DMSO (40 ml) and cooled. Sodium hydride (0.91 g, 80% suspension in oil) was added and the mixture was allowed to warm to room temperature. When the evolution of hydrogen had ceased 1-fluoro-3-nitrobenzene was added and the mixture was heated to 120° C. overnight. After cooling the reaction mixture was poured into ice-water and the crude product was filtered off. Purification was achieved by column chromatography on silica gel with ethyl acetate/petroleum ether (1:1) as the eluent. Yield 2.09 g, mp 175°-177° C.

Workup

  1. temperaturecooled
  2. additionwas added
  3. temperaturethe mixture was heated to 120° C. overnight
  4. temperatureAfter cooling the reaction mixture
  5. filtrationthe crude product was filtered off
  6. customPurification

Sources & evidence

ORD record
ord-53d9d2567d24473a853f91f496e0c200
Source dataset
uspto-grants-1996_09
Patent number
US05554630

Reaction notes

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