Water → HCID 54166724, compound

HRID 1770261Notes

Reaction equation

HRID 1770261 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:19]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1.[CH2:39]([C:43]1[NH:44][C:45]2[CH:51]=[C:50]([N:52]3[C:57](=[O:58])[CH2:56][C:55]([CH3:60])([CH3:59])[CH2:54][C:53]3=[O:61])[CH:49]=[CH:48][C:46]=2[N:47]=1)[CH2:40][CH2:41][CH3:42].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:39]([C:43]1[N:44]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:18]=[N:17][N:16]=3)=[CH:5][CH:4]=2)[C:45]2[CH:51]=[C:50]([N:52]3[C:53](=[O:61])[CH2:54][C:55]([CH3:60])([CH3:59])[CH2:56][C:57]3=[O:58])[CH:49]=[CH:48][C:46]=2[N:47]=1)[CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 962WaterHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 23665647Potassium tert-butoxideHCID 54263016HCID 54263016, compound

Product 1

HCID 54166724HCID 54166724, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.8 g (3.3 mMol) of 4'-bromomethyl-2-(1-triphenylmethyl-tetrazol-5-yl)-biphenyl are added to a solution of 1.04 g (3.3 mMol) of 2-n-butyl-5-(3,3-dimethyl-glutarimido)-benzimidazole and 425 mg (3.8 mMol) of potassium tert.-butoxide in 25 ml of dimethylsulphoxide. The mixture is stirred for 3 hours at ambient temperature, then stirred into 150 ml of water, extracted three times with 30 ml of ethyl acetate, then the organic extracts are dried and concentrated by evaporation. The residue obtained is purified by column chromatography (300 g of silica gel; eluant: ethyl acetate/petroleum ether (2:1)).

Workup

  1. extractionextracted three times with 30 ml of ethyl acetate
  2. customthe organic extracts are dried
  3. concentrationconcentrated by evaporation
  4. customThe residue obtained
  5. customis purified by column chromatography (300 g of silica gel; eluant: ethyl acetate/petroleum ether (2:1))

Sources & evidence

ORD record
ord-e02300af52c745f79a719276801bcf08
Source dataset
uspto-grants-1995_01
Patent number
US05385925

Reaction notes

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