Water → HCID 178458503, compound

HRID 2062471Notes

Reaction equation

HRID 2062471 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([NH2:6])=[N:2]1.[CH2:7]([O:10][CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)[CH:8]=[CH2:9].C([BH3-])#N.[Na+].O>C(O)(=O)C>[CH2:7]([O:10][CH:11]1[CH2:16][CH2:15][CH:14]([NH:6][C:3]2[NH:4][CH:5]=[N:1][N:2]=2)[CH2:13][CH2:12]1)[CH:8]=[CH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 184137294-(2-Propen-1-yloxy)cyclohexanoneHCID 178418311HCID 178418311, compound

Product 1

HCID 178458503HCID 178458503, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 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 reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%).

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 reaction mixture
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1f34177473c4ea48801248f6dd07a81
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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