Potassium Carbonate → 1,5-dihydro-5,5-dimethyl-2-propyl-1-[(2'-(triphenyl methyl tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one

HRID 21838Notes

Reaction equation

HRID 21838 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]2[N:25]([CH3:26])[N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:23]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:22]2[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:11][CH:10]=1>CN(C)C=O>[CH3:40][C:39]1([CH3:44])[N:22]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH:21]3[N:25]([CH3:26])[N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:23]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:22]3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:11][CH:10]=2)[C:21]([CH2:16][CH2:15][CH3:12])=[N:25][C:1]1=[O:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 543607154'-Bromomethyl-2-(triphenyl methyl tetrazol-5-yl)biphenyl

Product 1

HCID 199334831,5-dihydro-5,5-dimethyl-2-propyl-1-[(2'-(triphenyl methyl tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-oneYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium carbonate (500 mg, 3.7 mmol), 2-propyl-4-4-dimethyl-1H-imidazol-5(4H)-one (0.6 g, 3.9 mmol), and 4'-bromomethyl-2-(triphenyl methyl tetrazol-5-yl)biphenyl (1.08 g, 1.9 mmol) in dimethyl formamide (5 mL) was allowed to stir at room temperature overnight. The mixture was chromatographed over silica gel eluting with ethyl acetate-hexane to give 1,5-dihydro-5,5-dimethyl-2-propyl-1-[(2'-(triphenyl methyl tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]-4H-imidazol-4-one (70 mg, 14% ) M.S. m/e 631.5 (M+ +H) NMR (CDCl3 /TMS) δ0.88 (t, 3H, J=7 Hz, CH3), 1.38 (s, 6H, 2 CH3), 1.67 (m, 2H, CH2), 2.21 (t, 2H, J=7Hz, CH2), 4.56 (s, 2H, CH2), 6.92 (d, J= 7 Hz, 8H, Harom), 7.11 (d, J=7 Hz, 2H, Harom), 7.24-7.38 (m, 10H, Harom), 7.47 (m, 2H, Harom), 7.92 (m, 1H, Harom).

Workup

  1. customThe mixture was chromatographed over silica gel eluting with ethyl acetate-hexane

Sources & evidence

ORD record
ord-e7441d399bc6434c851036ded6765c8d
Source dataset
uspto-grants-1995_06
Patent number
US05424450

Reaction notes

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