Benzimidazole → HCID 3159973, compound

HRID 1471211Notes

Reaction equation

HRID 1471211 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[C:16]1([CH2:15][CH2:14][CH2:13][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydride

Product 1

HCID 3159973HCID 3159973, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask were added 5 g benzimidazole and 75 ml tetrahydrofuran under nitrogen and the solution was cooled to 10 C with stirring. 2.2 g Sodium hydride were added in small portions and the reaction was stirred for 10 minutes. 1-Bromo-3-phenylpropane was added and the reaction mixture was heated to 40 C for 5 hrs. After cooling to 5 C, the reaction was quenched with slow addition of 100 ml water. After the tetrahydrofuran was removed of by rotovap, the mixture was extracted with 100 ml ethyl acetate and washed with 25 ml water and the solvent was removed on the rotovap. The product was purified by column chromatography using 40% ethyl acetate in hexane resulting in a light yellow oil which crystallized in the freezer.

Workup

  1. temperaturethe solution was cooled to 10 C
  2. stirringthe reaction was stirred for 10 minutes
  3. temperaturethe reaction mixture was heated to 40 C for 5 hrs
  4. temperatureAfter cooling to 5 C
  5. customthe reaction was quenched with slow addition of 100 ml water
  6. customAfter the tetrahydrofuran was removed of by rotovap
  7. extractionthe mixture was extracted with 100 ml ethyl acetate
  8. washwashed with 25 ml water
  9. customthe solvent was removed on the rotovap
  10. customThe product was purified by column chromatography
  11. customcrystallized in the freezer

Sources & evidence

ORD record
ord-9d6f8ccc74434cc6ac6fad0b5f4f1217
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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