Acetonitrile → HCID 86748074, compound

HRID 248442Notes

Reaction equation

HRID 248442 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:33]3[N:37]=[CH:36][O:35][C:34]3=[S:38])=[CH:23][CH:22]=2)[C:7]([CH2:11][O:12][Si](C(C)(C)C)(C)C)=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(#N)C.C([O-])(O)=O.[Na+]>O>[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:33]3[N:37]=[CH:36][O:35][C:34]3=[S:38])=[CH:25][CH:26]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 131717904HCID 131717904, compound

Product 1

HCID 86748074HCID 86748074, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-[4'-[[2-butyl-4-chloro-5-(t-butyldimethylsilyloxymethyl)-1H-imidazol-1-yl]methyl][1,1'-biphenyl-2-yl]-1,3,4-oxadiazol-2[3H]-thione (100 mg) in 1:9 48% HF/acetonitrile (10 mL) was stirred at room temperature for 3 hours in a plastic flask. The reaction mixture was neutralized by the dropwise addition of saturated aqueous NaHCO3 (to pH 5) and was diluted with water. The resulting precipitate was collected by filtration and washed with water. Recrystallization from ethyl acetate gave pure 5-[4'-[[2-butyl-4-chloro-5-(hydroxymethyl)1H imidazol-1-yl]methyl][1,1'-biphenyl-2-yl]-1,3,4-oxadiazol-2[3H]-thione (40 mg, 50%), mp 193°-194° C. dec.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-597808b76d5949bb89e48866956bed93
Source dataset
uspto-grants-1993_05
Patent number
US05210204

Reaction notes

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