Imidazole → 1-Pent-4-ynylimidazole

HRID 1984100Notes

Reaction equation

HRID 1984100 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CC(=O)CC.O>[CH2:6]([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)[CH2:7][CH2:8][C:9]#[CH:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 12476209Pent-4-yn-1-yl methanesulfonate

Product 1

HCID 138653661-Pent-4-ynylimidazoleYield 53.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixure of pent-4-ynyl methanesulfonate (1.06 g), imidazole (534 mg) and K2CO3 (3.66 g) in 2-butanone (11 mL) was heated to reflux overnight. Work-up (DCM, H2O), drying (Na2SO4) and concentration gave 1-(pent-4-ynyl)-1H-imidazole (472 mg).

Workup

  1. temperatureto reflux overnight
  2. customdrying
  3. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-20d2c9679d214986a1a8419e960c9de1
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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