Acetonitrile → HCID 86748074, compound

HRID 1742226Notes

Reaction equation

HRID 1742226 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-53df52c5f6ef4c73a606af66afc768b9
Source dataset
uspto-grants-1994_08
Patent number
US05338737

Reaction notes

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