Ethanol → HCID 9926379, compound

HRID 1700131Notes

Reaction equation

HRID 1700131 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[C:8](=O)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:3][CH:2]=1.CCO.[CH2:24]([NH2:27])[CH2:25][NH2:26].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)=[N:27][CH:24]=[CH:25][N:26]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3301EthylenediamineHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 229487461-(Pyridin-4-yl)-2-[3-(trifluoromethyl)phenyl]ethane-1,2-dione

Product 1

HCID 9926379HCID 9926379, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Under Ar, a solution of 46 (2.3 g, 8.2 mmol) in abs. EtOH (100 mL) was treated with ethylene diamine (0.58 g, 9.6 mmol) and heated at 50° C. After 18 h, the solution was concentrated to dryness. The residue was partitioned between H2O and EtOAc (3×) and the organic extracts were dried, filtered and concentrated to dryness. The residue was treated with toluene (125 mL) and DDQ (3.8 g, 16.7 mmol) and then heated to 80° C. After 18 h, the reaction was concentrated to dryness. The residue was dry packed with silica gel (100 mL) and chromatographed on a Still column (80 mm). The product was eluted with EtOAc and the common fraction concentrated to dryness. The residue was treated with Et2O and ethanolic-HCl and concentrated to dryness. The residue was triturated from EtOAc and filtered to yield 100 mg of 47.

Workup

  1. concentrationthe solution was concentrated to dryness
  2. customThe residue was partitioned between H2O and EtOAc (3×)
  3. customthe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. temperatureheated to 80° C
  7. waitAfter 18 h
  8. concentrationthe reaction was concentrated to dryness
  9. customThe residue was dry
  10. customchromatographed on a Still column (80 mm)
  11. washThe product was eluted with EtOAc
  12. concentrationthe common fraction concentrated to dryness
  13. additionThe residue was treated with Et2O and ethanolic-HCl
  14. concentrationconcentrated to dryness
  15. customThe residue was triturated from EtOAc
  16. filtrationfiltered

Sources & evidence

ORD record
ord-f4293a89c8f349b886fe6129c274b60d
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

Loading…