Sodium Azide → 1-Benzyl-2-azidomethylbenzimidazole

HRID 568604Notes

Reaction equation

HRID 568604 reaction equation
Cl.[CH2:2]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18]Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O.O>[CH2:2]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:20]=[N+:21]=[N-:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 123777411-Benzyl-2-chloromethyl-1H-benzoimidazole hydrochloride

Product 1

HCID 146265071-Benzyl-2-azidomethylbenzimidazoleYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-Benzyl-2-chloromethylbenzimidazole hydrochloride (16 g, 0.055 mole) in N,N-dimethylformamide (80 ml) was stirred and a solution of sodium azide (17 g, 0.26 mole) in water (40 ml) was added. The resulting yellow solution was heated on a steam bath for 30 minutes, diluted with water (250 ml) and the crystalline product was filtered, dried in vacuo at room temperature, and recrystallized from 2-propanol to yield 10.5 g (73%) of product: mp 108°-110°.

Workup

  1. temperatureThe resulting yellow solution was heated on a steam bath for 30 minutes
  2. filtrationthe crystalline product was filtered
  3. customdried in vacuo at room temperature
  4. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-de2723fdab284c7ea8be4d28ea17ff2c
Source dataset
uspto-grants-1988_03
Patent number
US04728741

Reaction notes

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