4-Nitrobenzyl chloride → 4-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]aniline

HRID 2181071Notes

Reaction equation

HRID 2181071 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1>C1COCC1>[CH:1]([C:4]1[N:5]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 221212-(propan-2-yl)-1H-1,3-benzodiazoleHCID 24758Sodium hydride

Product 1

HCID 223927884-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-isopropylbenzimidazole (4.0 g, 25 mmol) in THF was treated with sodium hydride (1.00 g, 25 mmol, 60% dispersed in oil) under N2 atmosphere and stirred for 2 hr. 4-Chloromethyl-1-nitrobenzene (4.3 g, 25 mmol) was added and the reaction stirred for 16 hr. The reaction was worked by extraction from NaHCO3 with EtOAc×3, the combined organic layers were dried with MgSO4, filtered, and concentrated. This material was converted to the aniline as shown in Example 200. MS found: (M+H)=267.

Workup

  1. stirringthe reaction stirred for 16 hr
  2. extractionThe reaction was worked by extraction from NaHCO3 with EtOAc×3
  3. dry with materialthe combined organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-603c814a0c3f457bb1113056384d0dd0
Source dataset
uspto-grants-2005_05
Patent number
US06890915B2

Reaction notes

Loading…