1-Butanol → 6,7-Dichloro-2,3-dimethoxy-5-[3-(3-chlorophenyl)-5-methyl-4H-1,2,4-triazol-4-yl]quinoxaline

HRID 842677Notes

Reaction equation

HRID 842677 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][C:18](=S)[CH3:19])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([NH:27][NH2:28])=O.C(O)CCC>ClCCl.[Hg]=O>[Cl:1][C:2]1[C:3]([N:17]2[C:18]([CH3:19])=[N:28][N:27]=[C:25]2[C:24]2[CH:29]=[CH:30][CH:31]=[C:22]([Cl:21])[CH:23]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2

Participants

6

Reactant 3

HCID 2631-ButanolHCID 742893-ChlorobenzohydrazideHCID 226148756,7-Dichloro-2,3-dimethoxy-5-thioacetamidoquinoxaline

Product 1

HCID 226148706,7-Dichloro-2,3-dimethoxy-5-[3-(3-chlorophenyl)-5-methyl-4H-1,2,4-triazol-4-yl]quinoxalineYield 35.4%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6,7-dichloro-2,3-dimethoxy-5-thioacetamidoquinoxaline (250 mg, 0.753 mmol), 3-chlorobenzhydrazide (167 mg, 0.978 mmol), mercury(II) oxide (163 mg, 0.753 mmol), powdered 4 Å molecular sieves (175 mg) and n-butanol (7 mL) was heated under reflux for 18 hours. After being cooled, the mixture was filtered through ARBOCEL (trade mark) filter aid and the residue washed with dichloromethane. The filtrate was concentrated under reduced pressure to afford a green solid which was dissolved in dichloromethane, washed twice with 2M aqueous hydrochloric acid solution followed by brine, then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with dichloromethane:methanol (98:2, by volume) to give the title compound (120 mg, 35%) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter being cooled
  4. filtrationthe mixture was filtered through ARBOCEL (trade mark)
  5. filtrationfilter aid
  6. washthe residue washed with dichloromethane
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto afford a green solid which
  9. washwashed twice with 2M aqueous hydrochloric acid solution
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by flash chromatography on silica gel
  13. washeluting with dichloromethane:methanol (98:2, by volume)

Sources & evidence

ORD record
ord-792d7b03137842de8f13e55272fbbf41
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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