Water → HCID 19592437, compound

HRID 613520Notes

Reaction equation

HRID 613520 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][C:14]1[C:23]2[C:18](=[C:19]([NH:24][C:25](=[O:34])[C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:33])[CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[N:1]1([CH2:13][C:14]2[C:23]3[C:18](=[C:19]([NH:24][C:25](=[O:34])[C:26]4[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:33])[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 19592648HCID 19592648, compound

Product 1

HCID 19592437HCID 19592437, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of benzimidazole (26.5 mg) in N,N-dimethylformamide (1 ml) was added sodium hydride (60% in oil, 8.6 mg) in an ice bath, and the mixture was stirred at the same temperature for half an hour. To this mixture was added 4-bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline (80 mg) one portion, and the reaction mixture was stirred at the same temperature for half an hour and then at ambient temperature for one hour. Water was added thereto, and the resulting precipitate was collected by filtration. The solid was washed with hot 95% aqueous ethanol (1 ml) and allowed to cool to ambient temperature. The solid was collected by filtration and air-dried to give 4-(1H-benzimidazol-1-ylmethyl)-8-(2,6-dichlorobenzoylamino)quinoline (65 mg) as an off-white solid.

Workup

  1. stirringthe reaction mixture was stirred at the same temperature for half an hour
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe solid was washed with hot 95% aqueous ethanol (1 ml)
  4. filtrationThe solid was collected by filtration
  5. customair-dried

Sources & evidence

ORD record
ord-17d357a7c1834d308e34e54d141c6050
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…