Sodium Chloride → 4'-[(2-Ethoxy-4-methyl-6-(1-methyl-benzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-2-(2-triphenylmethyl-tetrazol-5-yl)-biphenyl

HRID 234039Notes

Reaction equation

HRID 234039 reaction equation
[CH2:1]([O:3][C:4]1[NH:5][C:6]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)=[CH:9][C:7]=2[N:8]=1)[CH3:2].CC(C)([O-])C.[K+].Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:44]2[N:45]=[N:46][N:47]([C:49]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:48]=2)=[CH:34][CH:33]=1.[Cl-].[Na+]>CS(C)=O>[CH2:1]([O:3][C:4]1[N:8]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]3[N:45]=[N:46][N:47]([C:49]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[N:48]=3)=[CH:36][CH:37]=2)[C:7]2[CH:9]=[C:10]([C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)[CH:11]=[C:12]([CH3:13])[C:6]=2[N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 108646215-(4'-(Bromomethyl)-1,1'-biphenyl-2-yl)-2-triphenylmethyl-2H-tetrazoleHCID 23665647Potassium tert-butoxideHCID 178467351HCID 178467351, compound

Product 1

HCID 199646024'-[(2-Ethoxy-4-methyl-6-(1-methyl-benzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-2-(2-triphenylmethyl-tetrazol-5-yl)-biphenyl

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 570 mg (1.86 mMol) of 2-ethoxy-4-methyl-6-(1-methyl-benzimidazol-2-yl)-benzimidazole in 20 ml of dimethylsulphoxide are added 224 mg (2.0 mMol) of potassium tert.butoxide and the mixture is stirred for 15 minutes at ambient temperature. Then 1.11 g (2.0 mMol) of 4'-bromomethyl-2-(2-triphenylmethyl-tetrazol-5-yl)-biphenyl are added and the mixture is stirred for a further 3 hours at ambient temperature. Then the mixture is stirred into about 50 ml of saturated sodium chloride solution, the crude product precipitated is suction filtered and purified by column chromatography (100 g silica gel; eluant: ethyl acetate/petroleum ether=4:1).

Workup

  1. stirringthe mixture is stirred for a further 3 hours at ambient temperature
  2. customthe crude product precipitated
  3. filtrationfiltered
  4. custompurified by column chromatography (100 g silica gel; eluant: ethyl acetate/petroleum ether=4:1)

Sources & evidence

ORD record
ord-dd3bdbecbd814e09b83c4c1b8d647ac7
Source dataset
uspto-grants-1997_01
Patent number
US05594003

Reaction notes

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