2-Phenylbenzimidazole → HCID 1542147, compound

HRID 495241Notes

Reaction equation

HRID 495241 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH2:19][CH2:20][CH3:21]>O1CCCC1>[C:1]1([C:7]2[N:8]([CH2:19][CH2:20][CH3:21])[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 128552-PhenylbenzimidazoleHCID 24758Sodium hydrideHCID 336431-Iodopropane2×

Product 1

HCID 1542147HCID 1542147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask were added 3.0 g 2-phenylbenzimidazole and 60 ml tetrahydrofuran and the mixture was cooled to 10 C under nitrogen. 0.41 g Sodium hydride were added in portions and the reaction mixture was stirred for 20 minutes, then cooled to 10 C. 3.1 g 1-iodopropane were added and the mixture was heated to 55 C for 16 hours. Another 0.8 g 1-iodopropane were added and the temperature was held at 55 C for two hours. The mixture was cooled to 22 C, quenched slowly with 40 ml water, extracted with ethyl acetate and washed with water. Following solvent removal, the product was purified by silica gel chromatography using straight 67% ethyl acetate, 24% hexane and 9% methanol. An oil was obtained.

Workup

  1. temperaturethe mixture was cooled to 10 C under nitrogen
  2. temperaturecooled to 10 C
  3. temperaturethe mixture was heated to 55 C for 16 hours
  4. waitthe temperature was held at 55 C for two hours
  5. temperatureThe mixture was cooled to 22 C
  6. customquenched slowly with 40 ml water
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. customFollowing solvent removal
  10. customthe product was purified by silica gel chromatography
  11. customAn oil was obtained

Sources & evidence

ORD record
ord-88f3655a3c7b4dabbf0bdfc3ab837786
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Reaction notes

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