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

HRID 232979Notes

Reaction equation

HRID 232979 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]3[N:15]=[C:16]([CH3:19])[O:17][CH:18]=3)=[CH:9][C:7]=2[N:8]=1)[CH2:2][CH3:3].CC(C)([O-])C.[K+].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[N:41]=[N:42][N:43]([C:45]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:44]=2)=[CH:30][CH:29]=1.[Cl-].[Na+]>CS(C)=O>[CH2:1]([C:4]1[N:8]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[N:41]=[N:42][N:43]([C:45]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:44]=3)=[CH:32][CH:33]=2)[C:7]2[CH:9]=[C:10]([C:14]3[N:15]=[C:16]([CH3:19])[O:17][CH:18]=3)[CH:11]=[C:12]([CH3:13])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 108646215-(4'-(Bromomethyl)-1,1'-biphenyl-2-yl)-2-triphenylmethyl-2H-tetrazoleHCID 23665647Potassium tert-butoxideHCID 178439854HCID 178439854, compound

Product 1

HCID 199645644'-[(2-n-Propyl-4-methyl-6-(2-methyl-oxazol-4-yl)-benzimidazol-1-yl)-methyl]-2-(2-triphenylmethyl-tetrazol-5-yl)-biphenyl

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2.8 g (11 mMol) of 2-n-propyl-4-methyl-6-(2-methyl-oxazol-4-yl)-benzimidazole and 1.7 g (15 mMol) of potassium tert.butoxide in 60 ml of dimethylsulphoxide is stirred for 15 minutes at ambient temperature. Then 6.0 g of (11 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 solution is stirred into about 150 ml of saturated sodium chloride solution, the crude product precipitated is suction filtered and purified by column chromatography (500 g of silica gel; eluant: petroleum ether/ethyl acetate=1:1)

Workup

  1. customthe crude product precipitated
  2. filtrationfiltered
  3. custompurified by column chromatography (500 g of silica gel; eluant: petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1618e925044241448eaa2c552d8dda9d
Source dataset
uspto-grants-1997_01
Patent number
US05591762

Reaction notes

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