Propargyl bromide → HCID 14851947, compound

HRID 1032770Notes

Reaction equation

HRID 1032770 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[O:17].C(Br)C#C>CN(C)C=O>[CH3:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:5]=[CH:2][C:3]=2[N:10]([CH2:11][C:16]#[CH:15])[C:9]1=[O:17]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 14851947HCID 14851947, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

potassium tert.-butoxide, 2.1 g (18.5 mmol). was added to a solution of 2.5 g (16.9 mmol) of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one in 25 ml of dimethylformamide. After stirring under nitrogen for 15 minutes, 2.21 g (18.5 mmol) of propargyl bromide was added and the mixture was stirred at room temperature for 30 minutes. It was diluted with ice-water and the precipitate was filtered off washed with water and sucked dry. The crude product was passed over silica gel using 10% (v/v) of ethyl/acetate in methylene chloride for elution. Crystallization from ethyl acetate/hexane gave colorless crystals of 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazole-2-one with m.p. 110°-112°.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customsucked dry
  5. washThe crude product was passed over silica gel using 10% (v/v) of ethyl/acetate in methylene chloride for elution
  6. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-22cfeace31c945419ddf3a848b3ddf4e
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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