Water → HCID 15248974, compound

HRID 1532620Notes

Reaction equation

HRID 1532620 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[CH3:6][C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[H-].[Na+].O>CN(C=O)C>[CH2:1]([N:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[C:7]1[CH3:6])[CH:3]1[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 119842-MethylbenzimidazoleHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 15248974HCID 15248974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Epibromohydrin (1.0 g, 7.6 mmole) was added to a stirred solution of 2-methylbenzimidazole (1.0 g, 7.6 mmole) and sodium hydride (0.3 g, 7.6 mmole) in anhydrous DMF (20 ml), and the mixture was heated at 60° C. under nitrogen for 0.5 hours. Water (100 ml) was added and the product extracted into CH2Cl2 (3×25 ml). The combined organics were washed with water (25 ml), brine (25 ml) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave the crude product as a light yellow colored oil (1.4 g). This was purified by flash silica gel chromatography (10% methanol in CH2Cl2) to afford the titled product as a light oil (0.64 g, 45% yield).

Workup

  1. extractionthe product extracted into CH2Cl2 (3×25 ml)
  2. washThe combined organics were washed with water (25 ml), brine (25 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customgave the crude product as a light yellow colored oil (1.4 g)
  6. customThis was purified by flash silica gel chromatography (10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-e3024d6a37974f44bf9a8cf56491a03d
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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