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 977490Notes

Reaction equation

HRID 977490 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-9b5a8e800dd64bc2b6bd165bd4b3fe07
Source dataset
uspto-grants-1997_03
Patent number
US05614519

Reaction notes

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