Ammonia → 1-prop-2-ynylbenzimidazole

HRID 2377282Notes

Reaction equation

HRID 2377282 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:10][C:11](C)([O-])[CH3:12].[K+].O1CCCC1.C(Br)C#C.C(=O)(O)[O-].[Na+].N>CN(C)C=O>[CH2:12]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)[C:11]#[CH:10]

Participants

8

Reactant 6

HCID 222AmmoniaHCID 5798BenzimidazoleHCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20483131-prop-2-ynylbenzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-benzimidazole (1.0 g, 8.46 mmol) in N,N-dimethylformamide (12 mL) was added a 1M solution of potassium tert-butoxide in tetrahydrofuran (8.04 mL, 8.04 mmol). The solution was stirred at room temperature for about 10 min, before propargyl bromide (0.940 mL, 8.46 mmol) was added dropwise. The solution was stirred at room temperature for about 30 min, poured into a cooled saturated aqueous solution of sodium bicarbonate and was extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated under vacuum to provide Example 648. MS (DCI-NH3): m/z 157 (M+H)+.

Workup

  1. additionwas added dropwise
  2. extractionwas extracted with dichloromethane
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto provide Example 648

Sources & evidence

ORD record
ord-2e28ce4da4a74f48a05d63825852949a
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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