5-Nitrobenzimidazole → ethyl 2-(5-nitro-1H-benzimidazol-1-yl)octanoate

HRID 743878Notes

Reaction equation

HRID 743878 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:16]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]([CH:16]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 71955-NitrobenzimidazoleHCID 24758Sodium hydrideHCID 95580Ethyl 2-bromooctanoate

Product 1

HCID 21468840ethyl 2-(5-nitro-1H-benzimidazol-1-yl)octanoateYield 22.9%

Procedure

5-Nitrobenzimidazole (0.109 moles, 17.8 g.) was reacted with sodium hydride (0.122 moles, 4.9 g of 60% in mineral oil) and ethyl 2-bromooctanoate (0.102 moles, 22 ml) as in Example 11 to produce a mixture of the 5 and 6 isomer. The isomers were separated to yield 7.8 g of ethyl 2-(5-nitro-1H-benzimidazol-l-yl)octanoate.

Workup

  1. customto produce
  2. additiona mixture of the 5 and 6 isomer
  3. customThe isomers were separated

Sources & evidence

ORD record
ord-bb1d38eaa71045d18e5ecd279e6753dd
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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