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

HRID 842668
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HRID 842668 반응식
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
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참가 물질

6

반응물 4

HCID 222AmmoniaHCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 226148716,7-Dichloro-2,3-dimethoxy-5-(N-methylcarbamoyl)quinoxaline

생성물 1

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

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7671fda7fd4049289780734104922aef
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06376490B1

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