Triethylamine → HCID 22614866, compound

HRID 842671Notes

Reaction equation

HRID 842671 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][C:8]1[C:9]([C:23](=O)[NH:24][CH2:25][CH:26]=[CH2:27])=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]=[C:13]([O:19][CH3:20])[C:12]([O:21][CH3:22])=[N:11]2.[CH:29]([NH:31][NH2:32])=O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:7][C:8]1[C:9]([C:23]2[N:24]([CH2:25][CH:26]=[CH2:27])[CH:29]=[N:31][N:32]=2)=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]=[C:13]([O:19][CH3:20])[C:12]([O:21][CH3:22])=[N:11]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 24819Phosphorus pentachlorideHCID 22614852HCID 22614852, compound

Product 1

HCID 22614866HCID 22614866, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus pentachloride (0.67 g, 3.22 mmol) was added to a stirred suspension of 6,7-dichloro-2,3-dimethoxy-5-(N-allylcarbamoyl)quinoxaline (Preparation 18, 1.0 g, 2.93 mmol) in toluene (40 mL) at room temperature and then heated under reflux for 1 hour. After being cooled, formylhydrazine (0.585 g, 8.79 mmol) and triethylamine (0.592 g, 8.79 mmol) were added and the mixture heated under reflux for 1 hour. After being cooled, the mixture was partitioned between ethyl acetate (60 mL) and 10% w/w aqueous potassium carbonate solution (60 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (2×40 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using toluene:ethyl acetate (1:0 changing to 1:1, by volume) to afford 6,7-dichloro-2,3-dimethoxy-5-(4-allyl-4H-1,2,4-triazol-3-yl)quinoxaline (0.112 g, 10%) as a white solid, mp 206-208° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter being cooled
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 1 hour
  6. temperatureAfter being cooled
  7. customthe mixture was partitioned between ethyl acetate (60 mL) and 10% w/w aqueous potassium carbonate solution (60 mL)
  8. customThe phases were separated
  9. extractionthe aqueous phase extracted with ethyl acetate (2×40 mL)
  10. dry with materialThe combined organic extracts were dried (MgSO4)
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-8a315233682e416caddbb71d3ff0f46b
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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