Ethylenediamine → HCID 18317241, compound

HRID 1700130Notes

Reaction equation

HRID 1700130 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8](=O)[C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH:5]=[CH:4][N:3]=1.[CH2:22]([NH2:25])[CH2:23][NH2:24].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CCO>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)=[N:25][CH:22]=[CH:23][N:24]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 18317244HCID 18317244, compound

Product 1

HCID 18317241HCID 18317241, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Under Ar, a solution of 42 (3.35 g, 11.3 mmol) in EtOH (150 mL) was treated with ethylene diamine (0.9 g, 15 mmol) and heated at 50° C. After 3 h, the reaction was concentrated to dryness and the residue was partitioned between H2O and EtOAc (3×). The combined organic extracts were dried, filtered and concentrated to dryness. The residue was dissolved in toluene (230 mL) and reacted with DDQ (4.0 g, 17.6 mmol). After 18 h at room temperature, the reaction was heated at 60° C. for 2 h then treated with additional DDQ (1.0 g) and heated at 80° C. for 5 h. The reaction was then dry packed with silica gel (70 g) and chromatographed on a Still column (80 mm). The product was eluted with 30% EtOAc-hexanes to yield 2.85 g of 43.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customthe residue was partitioned between H2O and EtOAc (3×)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was dissolved in toluene (230 mL)
  7. waitAfter 18 h at room temperature
  8. temperaturethe reaction was heated at 60° C. for 2 h
  9. temperatureheated at 80° C. for 5 h
  10. customThe reaction was then dry
  11. customchromatographed on a Still column (80 mm)
  12. washThe product was eluted with 30% EtOAc-hexanes

Sources & evidence

ORD record
ord-16785626cddb4d4d8c422a1c746528d1
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

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