Triethylamine → HCID 178434758, compound

HRID 1293138Notes

Reaction equation

HRID 1293138 reaction equation
[CH3:1][C:2](=O)[CH:3]([S:7][C:8]1[N:12]=[CH:11][NH:10][N:9]=1)[C:4](=[O:6])[CH3:5].Cl.NO.C([N:19](CC)CC)C>C(O)C>[CH3:1][C:2]1[C:3]([S:7][C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([CH3:5])[O:6][N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 178473690HCID 178473690, compound

Product 1

HCID 178434758HCID 178434758, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(2,4-pentanedion-3-yl)thio-1H-1,2,4-triazole (2 g), hydroxylamine hydrochloride (0.7 g), triethylamine (1.4 ml) and ethanol (10 ml) was heated and stirred for 5 hours on an oil bath at 100° C. The reaction solution was concentrated under reduced pressure, and then extracted with ethyl acetate-water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to a silica-gel column chromatography with 10 to 30% (20% 2-propanol/ethyl acetate)/hexane, followed by recrystallization in ethyl acetate-hexane to yield the title compound (440 mg).

Workup

  1. temperaturewas heated
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate-water
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customfollowed by recrystallization in ethyl acetate-hexane

Sources & evidence

ORD record
ord-cc14cea576b8429bbe0f79f74156484d
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

Loading…