Tetrahydrofuran → 6,7-Dichloro-2,3-dimethoxyquinoxaline

HRID 842663Notes

Reaction equation

HRID 842663 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:14](Cl)=[N:13][C:12]2[C:7](=[CH:8][C:9]([Cl:17])=[C:10]([Cl:16])[CH:11]=2)[N:6]=1.[O:18]1[CH2:22]CCC1>CO>[Cl:17][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[Cl:16])[N:13]=[C:14]([O:2][CH3:1])[C:5]([O:18][CH3:22])=[N:6]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 40971682,3,6,7-TetrachloroquinoxalineHCID 10942334Sodium Methoxide2×

Product 1

HCID 120471106,7-Dichloro-2,3-dimethoxyquinoxalineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium methoxide (25% wt/v in methanol, 190 mL, 880 mmol) was added dropwise to a stirred suspension of 2,3,6,7-tetrachloroquinoxaline (106 g, 400 mmol) in methanol (1400 mL) at room temperature under nitrogen. After 3 days, a solution of sodium methoxide (25% wt/v in methanol, 40 mL, 190 mmol) was added, followed by tetrahydrofuran (300 mL). The reaction mixture was heated under reflux for 5 minutes, cooled, concentrated to a small volume under reduced pressure and poured into water (500 mL). The precipitate was collected by filtration and washed with water to afford the title compound (97 g, 95%) as a pink solid, mp 144-146° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 minutes
  3. temperaturecooled
  4. concentrationconcentrated to a small volume under reduced pressure
  5. additionpoured into water (500 mL)
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-8c2ca6322c4b48629256bf370e501da0
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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