Dimethylformamide → HCID 22508792, compound

HRID 2229467Notes

Reaction equation

HRID 2229467 reaction equation
CN(C)C=O.[H-].[Na+].[Cl:8][C:9]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:10]=1[CH2:11][N:12]1[C:16]2[CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH3:26].[CH2:32](Br)[CH2:33][CH2:34][CH3:35]>C(OCC)(=O)C.O>[CH2:32]([O:31][C:29]1[CH:28]=[CH:27][C:10]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[CH3:26])=[C:9]([Cl:8])[CH:30]=1)[CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 225087681-(2-Chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole

Product 1

HCID 22508792HCID 22508792, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-dimethylformamide (5 ml) was added to 60% sodium hydride (0.20 g, oily). Crystals of 1-(2-chloro-4-hydroxybenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (0.80 g) were added gradually thereto at room temperature. After stirring for 1 hour at room temperature, n-butyl bromide (0.28 g, 4.14 mmol) was added to the mixture. After further stirring for 15 hours at room temperature, water and subsequently ethyl acetate were added to the solution to effect extraction. The organic layer was separated, washed twice with water, and concentrated to obtain 0.62 g of oil.

Workup

  1. customat room temperature
  2. stirringAfter further stirring for 15 hours at room temperature
  3. customThe organic layer was separated
  4. washwashed twice with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6a10fbc600048948176066764b3d24c
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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