Water → HCID 15585274, compound

HRID 1388158Notes

Reaction equation

HRID 1388158 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:11]([O:14][CH2:15][CH2:16]Br)[C:12]#[CH:13].[OH-].[Na+].O>CN(C)C=O>[Cl:1][C:2]1[N:6]([CH2:16][CH2:15][O:14][CH2:11][C:12]#[CH:13])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 785722-ChlorobenzimidazoleHCID 2879251-Propyne, 3-(2-bromoethoxy)-

Product 1

HCID 15585274HCID 15585274, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Chlorobenzimidazole (30.0 g) and 2-bromoethyl propargyl ether (41.0 g) are dissolved in N,N-dimethylformamide (300 ml), and thereto is added a 25% aqueous sodium hydroxide (40.0 g), and the mixture is stirred at 60° C. for 4 hours. Water (700 ml) is added to the reaction mixture, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue is distilled under reduced pressure to give 2-chloro-1-[2-(propargyloxy)ethyl]benzimidazole (24.5 g) as a colorless oily substance, b.p. 158°-160° C./1.2 mmHg.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. distillationThe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-8ec87a3ec5aa4400ae44cac223eb8321
Source dataset
uspto-grants-1984_02
Patent number
US04430343

Reaction notes

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