Einecs 211-027-4 → HCID 178450063, compound

HRID 480446Notes

Reaction equation

HRID 480446 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]#[N:41])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].[Cl-].[NH+]1C=CC=CC=1.C([O-])(O)=O.[Na+]>CO.C(Cl)(Cl)Cl>[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]#[N:41])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 69401Einecs 211-027-4HCID 516892Sodium BicarbonateHCID 18769121HCID 18769121, compound

Product 1

HCID 178450063HCID 178450063, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthonitrile (1.40 g) and pyridinium chloride (606 mg) in methanol-CHCl3 (1:1, 8 mL) was heated at 60° C. for 2 h. The reaction mixture was neutralized with aq. NaHCO3 solution and concentrated. The residue was extracted with ethanol, and the extract was purified by silica gel chromatography (eluent; dichloromethane:MeOH=30:1→10:1). Crystallization from ethyl acetate gave the titled compound (737 mg) as a colorless powder.

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with ethanol
  3. customthe extract was purified by silica gel chromatography (eluent; dichloromethane:MeOH=30:1→10:1)
  4. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cee6f9c5411d4713b0922e9de2944043
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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