Ammonia → 6,7-Dichloro-2,3-dimethoxy-5-(1-methyl-1H-tetrazol-5-yl)quinoxaline

HRID 842668Notes

Reaction equation

HRID 842668 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][C:8]1[C:9]([C:23](=O)[NH:24][CH3:25])=[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.C[Si]([N:31]=[N+:32]=[N-:33])(C)C.N>C1(C)C=CC=CC=1>[Cl:7][C:8]1[C:9]([C:23]2[N:24]([CH3:25])[N:33]=[N:32][N:31]=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 222AmmoniaHCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 226148716,7-Dichloro-2,3-dimethoxy-5-(N-methylcarbamoyl)quinoxaline

Product 1

HCID 226148996,7-Dichloro-2,3-dimethoxy-5-(1-methyl-1H-tetrazol-5-yl)quinoxalineYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorous pentachloride (0.136 g, 0.65 mmol) was added to a solution of 6,7-dichloro-2,3-dimethoxy-5-(N-methylcarbamoyl)quinoxaline (Preparation 7, 0.197 g, 0.62 mmol) in toluene (7 mL) and the mixture was heated under reflux under nitrogen for 1 hour. The reaction was cooled to room temperature and trimethylsilyl azide (123 μL, 0.107 g, 0.93 mmol) was added. After stirring at room temperature for 18 hours, dilute aqueous ammonia solution (20 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with dichloromethane to give the title compound (0.080 g, 38%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under nitrogen for 1 hour
  3. extractionthe mixture was extracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7671fda7fd4049289780734104922aef
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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