Tetrahydrofuran → HCID 86681574, compound

HRID 339431Notes

Reaction equation

HRID 339431 reaction equation
[CH3:1][S-:2].[Na+].O1CCCC1.[CH:9]([O:12][N:13]=[C:14]([N:26]1[CH:30]=[N:29][CH:28]=[N:27]1)[C:15](=[N:21][O:22][CH:23]([CH3:25])[CH3:24])N1C=NC=N1)([CH3:11])[CH3:10]>O>[CH3:1][S:2][C:15](=[N:21][O:22][CH:23]([CH3:25])[CH3:24])[C:14]([N:26]1[CH:30]=[N:29][CH:28]=[N:27]1)=[N:13][O:12][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4378561Sodium methanethiolateHCID 86681575HCID 86681575, compound

Product 1

HCID 86681574HCID 86681574, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium thiomethoxide was added to 5 ml of a tetrahydrofuran solution (which was under heating and refluxing) containing 0.35 g (1.14 mmol) of the 1,2-diisopropoxyimino-1,2-bis(1H-1,2,4-triazol-1-yl)ethane produced in Example 6, with confirming a reaction by thin-layer chromatography. Then, stirring was conducted for 5 hours. The reaction mixture was cooled to room temperature and poured into water, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2) to obtain 0.17 g (yield: 52%) of a title compound.

Workup

  1. customa reaction by thin-layer chromatography
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-f616321dc80e47b89899a43f20c644df
Source dataset
uspto-grants-2014_11
Patent number
US08895035B2

Reaction notes

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