Hydrochloric Acid → HCID 9802164, compound

HRID 842661Notes

Reaction equation

HRID 842661 reaction equation
[Cl:1][C:2]1[C:3]([N:17]2[C:21]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:20][N:19]=[C:18]2[CH2:28][O:29][CH3:30])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13]C)[C:6]([O:15]C)=[N:5]2.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([N:17]2[C:21]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:20][N:19]=[C:18]2[CH2:28][O:29][CH3:30])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6](=[O:15])[NH:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22614877HCID 22614877, compound

Product 1

HCID 9802164HCID 9802164, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (±)-6,7-dichloro-2,3-dimethoxy-5-[3-methoxymethyl-5-(3-pyridyl)-4H-1,2,4-triazol-4-yl]quinoxaline (3.0 g, 6.7 mmol), 2M aqueous hydrochloric acid solution (10 mL) and 1,4-dioxane (50 mL) was heated under reflux for 9 hours, cooled, and concentrated under reduced pressure. The residue was dissolved in 1M aqueous sodium hydroxide solution and acidified to pH 4.5 with concentrated hydrochloric acid to afford a thick white precipitate. This was collected by filtration and washed with water to give (±)-6,7-dichloro-5-[3-methoxymethyl-5-(3-pyridyl)-4H-1,2,4-triazol-4-yl]-2,3(1H,4H)-quinoxalinedione (2.0 g, 68%) as an off-white solid, mp 230-232° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 9 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 1M aqueous sodium hydroxide solution
  6. customto afford a thick white precipitate
  7. filtrationThis was collected by filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-a348872105414bcf882026071273be65
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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