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 1450590Notes

Reaction equation

HRID 1450590 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-9f9177652ca847158b0ac758fed9bdd5
Source dataset
uspto-grants-1997_02
Patent number
US05602127

Reaction notes

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