Benzimidazole → N-benzimidazolyl-1,2-propanediol

HRID 747324

Reaction equation

HRID 747324 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.Br[CH2:11][CH:12]([OH:15])[CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:1]1([CH:13]([OH:14])[CH:12]([OH:15])[CH3:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 208273-Bromo-1,2-propanediol

Product 1

HCID 22018573N-benzimidazolyl-1,2-propanediolYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzimidazole (590 mg, 5.0 mmol) and 3-bromo-1,2-propanediol (0.52 mL, 6.0 mmol) were dissolved in anhydrous acetonitrile (50 mL) and dry potassium carbonate (2.07 g, 15 mmol) was added. The solution was then heated to reflux for 3 days. Upon cooling the mixture was filtered and the filtrates were concentrated, giving the desired N-benzimidazolyl-1,2-propanediol (0.66 g, 69%) as a pale yellow solid. 1H NMR (CDCl3) δ 3.60 (m, 2H), 3.78 (m, 2H), 4.17 (m, 1H), 4.27 (m, 2H), 7.25 (m, 2H), 7.42 (d, 1H, J=6 Hz), 7.67 (d, 1H, J=6 Hz), 7.87 (s, 1H).

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux for 3 days
  3. temperatureUpon cooling the mixture
  4. filtrationwas filtered
  5. concentrationthe filtrates were concentrated

Sources & evidence

ORD record
ord-71fe93991ea84866aba847f5d131cb59
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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