2-Phenylbenzimidazole → (+/-)1-(3,7-Dimethyl-6-octen-1-yl)-2-phenylbenzimidazole

HRID 1606752Notes

Reaction equation

HRID 1606752 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+].Br[CH2:19][CH2:20][CH:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]>O1CCCC1.CN(C)C=O>[CH3:28][CH:21]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:20][CH2:19][N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 128552-PhenylbenzimidazoleHCID 24758Sodium hydrideHCID 43282458-Bromo-2,6-dimethyloct-2-ene

Product 1

HCID 21544647(+/-)1-(3,7-Dimethyl-6-octen-1-yl)-2-phenylbenzimidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a flask equipped with a stirrer, condenser and nitrogen inlet tube, there is added 90 ml. of anhydrous tetrahydrofuran, 30 ml. of anhydrous dimethylformamide and 9.7 g. (0.05 mole) of 2-phenylbenzimidazole. The resulting system is then blanketed with nitrogen, stirring is initiated and 2.2 g. (0.053 mole) of 57% sodium hydride mineral oil dispersion is added in one portion. The mixture is then heated to 50° for about 2 hours. After cooling to room temperature, a solution of 12.0 g. (0.053 mole) of (±) 1-bromo-3,7-dimethyl-6-octene in 50 ml. of dry tetrahydrofuran is added dropwise. The resulting mixture is stirred overnight at room temperature and the resultant salts are removed by filtration. The filtrate is concentrated in vacuo. The resultant oil is dissolved in chloroform and chromatographed on silica gel using methylenechloride as the eluant to give (±)1-(3,7-dimethyl-6-octen-1-yl)-2-phenylbenzimidazole, NMR (CDCl3) δ0.72-2.18 (16H, complex multiplet, ##EQU1## 4.23 (2H, triplet, J=7cps, CH2N), 5.00 (1H, triplet, J=7cps, HC=C), 7.13-7.95 (9H, multiplet, C6H5 and C6H4). Anal. Calcd. for C23H28N2 :C, 83.1; H, 8.5; N, 8.4. Found:C, 83.3; H, 8.8; N, 8.0.

Workup

  1. customIn a flask equipped with a stirrer, condenser and nitrogen inlet tube
  2. additionthere is added 90 ml
  3. temperatureThe mixture is then heated to 50° for about 2 hours
  4. stirringThe resulting mixture is stirred overnight at room temperature
  5. customthe resultant salts are removed by filtration
  6. concentrationThe filtrate is concentrated in vacuo
  7. dissolutionThe resultant oil is dissolved in chloroform
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-6b6fa82edf064d79a302270caf57c2db
Source dataset
uspto-grants-1976_04
Patent number
US03953600

Reaction notes

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