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Sodium hydride → 5-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole

HRID 397820
Notes
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Reaction equation

HRID 397820 reaction equation
[H-].[Na+].[C:3]1([C:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]2[C:14]3[CH2:15][CH2:16][CH:17]([CH2:19][OH:20])[CH2:18][C:13]=3[N:12]=[CH:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C3CC(CO)CCC=3N=C2)C=CC=CC=1.[O:63]([C:70]1[CH:77]=[CH:76][CH:75]=[CH:74][C:71]=1[CH2:72]Br)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[O:63]([C:70]1[CH:77]=[CH:76][CH:75]=[CH:74][C:71]=1[CH2:72][O:20][CH2:19][CH:17]1[CH2:16][CH2:15][C:14]2[N:10]([C:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:11]=[N:12][C:13]=2[CH2:18]1)[C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 226754691-(Bromomethyl)-2-phenoxybenzeneHCID 23512761(3-(triphenylmethyl)-4,5,6,7-tetrahydro-3H-benzimidazol-5-yl)methanolHCID 23512763(1-(triphenylmethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl)-methanol

Product 1

HCID 230012495-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 60% suspension of sodium hydride in mineral oil (4.1 g, 101 mmol) was added to a solution of a mixture of (1-(triphenylmethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl)-methanol and (3-(triphenylmethyl)-4,5,6,7-tetrahydro-3H-benzimidazol-5-yl)methanol (2.0 g, 5.1 mmol) in THF (8 ml). When the reaction had ceased tetrabutylammonium iodide (0.10 g, 0.25 mmol) and a solution of 2-phenoxybenzyl bromide (1.5 g, 5.6 mmol) in THF (5 ml) were added successively. The reaction mixture was stirred for 16 h. Water (100 ml) was added carefully. The mixture was extracted with ethyl acetate (3×60 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (gradient from 50:50 to 100:0) as eluent, to give 1.21 g of 5-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole and 5-((2-phenoxybenzyloxy)methyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×60 ml)
  2. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (100 ml)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (90 g)

Sources & evidence

ORD record
ord-08500b7de324408a822b2ea0d2de0cfa
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610721B2

Reaction notes

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