Water → HCID 178469004, compound

HRID 1412268Notes

Reaction equation

HRID 1412268 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.O=[C:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1.C([BH3-])#N.[Na+].O>C(O)(=O)C>[N:1]1[N:2]=[C:3]([NH:6][CH:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[NH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5003444Sodium cyanoborohydrideHCID 178418311HCID 178418311, compound

Product 1

HCID 178469004HCID 178469004, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution (200 mL) of 1H-1,2,4-triazol-3-amine (11 g) and ethyl 4-oxocyclohexanecarboxylate (28 g) in acetic acid was added sodium cyanoborohydride (35 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (13 g, 40%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe obtained residue was poured into saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1)
  4. extractionThe obtained extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-97aa2dad2ce8473690c257a2893bd19c
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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