Dimethylformamide → 5-Methoxy-3-methyl-1-(3-methyl-3-nitro-butyl)-1,3-dihydro-benzimidazol-2-one

HRID 33392Notes

Reaction equation

HRID 33392 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:15]=[CH:14][C:8]2[N:9]([CH3:13])[C:10](=[O:12])[NH:11][C:7]=2[CH:6]=1.ICC[CH2:19][C:20]([CH3:25])([N+:22]([O-:24])=[O:23])[CH3:21].[CH3:26]N(C=O)C>O>[CH3:3][O:4][C:5]1[CH:15]=[CH:14][C:8]2[N:9]([CH2:13][CH2:19][C:20]([CH3:25])([N+:22]([O-:24])=[O:23])[CH3:21])[C:10](=[O:12])[N:11]([CH3:26])[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 99430631-Iodo-4-methyl-4-nitro-pentaneHCID 213212535-methoxy-1-methyl-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 671887485-Methoxy-3-methyl-1-(3-methyl-3-nitro-butyl)-1,3-dihydro-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.1 g (28 mmol) 60% sodium hydride are added to 2.5 g (14 mmol) 5-methoxy-1-methyl-1,3-dihydro-benzimidazol-2-one in 30 mL DMF while being cooled with the ice bath. After 30 minutes a solution of 1-iodo-4-methyl-4-nitro-pentane in 20 mL DMF is piped in and the mixture is stirred overnight. It is diluted with water and extracted with ethyl acetate. The combined organic phases are washed with water, dried and evaporated down. The solid remaining is stirred with diethyl ether.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. customdried
  4. customevaporated down
  5. stirringThe solid remaining is stirred with diethyl ether

Sources & evidence

ORD record
ord-d35fe270f68d4d36ba671ea26580a9ec
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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