Tetrahydrofuran → 1-Phenyl-1H-benzoimidazole

HRID 495240Notes

Reaction equation

HRID 495240 reaction equation
C[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].I[CH2:14][CH2:15][CH3:16].O1C[CH2:20][CH2:19][CH2:18]1>>[C:15]1([N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=[CH:2]2)[CH:16]=[CH:20][CH:19]=[CH:18][CH:14]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 119842-MethylbenzimidazoleHCID 24758Sodium hydrideHCID 336431-Iodopropane

Product 1

HCID 6066691-Phenyl-1H-benzoimidazole

Procedure

To a flask were added 2.0 g 2-methylbenzimidazole and 40 ml tetrahydrofuran and the mixture was cooled to 10 C under nitrogen. 0.9 g Sodium hydride were added in portions and the reaction mixture was stirred for 20 minutes. 3.9 g 1-iodopropane were added and the mixture was heated to 45 C for 6 hours. The mixture was quenched slowly with 40 ml water, extracted twice with ethyl acetate and washed with water. Following solvent removal, the product was purified by silica gel chromatography using pure ethyl acetate to 5% methanol in ethyl acetate. A pale yellow oil was obtained.

Workup

  1. temperaturethe mixture was cooled to 10 C under nitrogen
  2. temperaturethe mixture was heated to 45 C for 6 hours
  3. customThe mixture was quenched slowly with 40 ml water
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water
  6. customFollowing solvent removal
  7. customthe product was purified by silica gel chromatography
  8. customA pale yellow oil was obtained

Sources & evidence

ORD record
ord-d4dfe13277e94937804cf49adf770927
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Reaction notes

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