Sodium hydride → 5-Fluoro-1-methyl-3-(4-methyl-4-nitro-pentyl)-1,3-dihydro-benzimidazol-2-one

HRID 33394Notes

Reaction equation

HRID 33394 reaction equation
[H-].[Na+].I[CH2:4][CH2:5][CH2:6][C:7]([CH3:12])([N+:9]([O-:11])=[O:10])[CH3:8].[F:13][C:14]1[CH:24]=[CH:23][C:17]2[N:18]([CH3:22])[C:19](=[O:21])[NH:20][C:16]=2[CH:15]=1>CN(C=O)C>[F:13][C:14]1[CH:24]=[CH:23][C:17]2[N:18]([CH3:22])[C:19](=[O:21])[N:20]([CH2:4][CH2:5][CH2:6][C:7]([CH3:12])([N+:9]([O-:11])=[O:10])[CH3:8])[C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 99430631-Iodo-4-methyl-4-nitro-pentaneHCID 220286845-Fluoro-1-methyl-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 671887105-Fluoro-1-methyl-3-(4-methyl-4-nitro-pentyl)-1,3-dihydro-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

First of all 0.624 g (13.9 mmol) 60% sodium hydride and then, with cooling, 4.6 g (17.8 mmol) 1-iodo-4-methyl-4-nitro-pentane in 10 mL DMF are added to a solution of 2.1 g (12.6 mmol) 5-fluoro-1-methyl-1,3-dihydro-benzimidazol-2-one in DMF. The reaction mixture is stirred overnight at ambient temperature, then poured onto water and extracted with diethyl ether. The organic phases are evaporated down and the residue is recrystallised from isopropylether. Yield: 1.8 g (48%); mass spectroscopy [M+H]+=296.

Workup

  1. additionpoured onto water
  2. extractionextracted with diethyl ether
  3. customThe organic phases are evaporated down
  4. customthe residue is recrystallised from isopropylether

Sources & evidence

ORD record
ord-d23e08876add4f53a84e1a2e71d7f132
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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