Dichloromethane → 2-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole

HRID 79457노트

반응식

HRID 79457 반응식
C([N:4]([C:6](=O)[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[C:10]([Br:20])=[N:9]1)[NH2:5])(=O)C.[P+3]=[S:23].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl.[CH2:33]1[CH2:37]OCC1>>[Br:20][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[N:8]([CH2:7][C:6]2[S:23][C:37]([CH3:33])=[N:5][N:4]=2)[N:9]=1

참가 물질

6

반응물 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 70814862N-acetyl-2-(3-bromo-4-nitro-1H-indazol-1-yl)acetohydrazideHCID 178527688HCID 178527688, 화합물

생성물 1

HCID 672601402-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole

실험 절차

A suspension of N-acetyl-2-(3-bromo-4-nitro-1H-indazol-1-yl)acetohydrazide (0.4 g) in anhydrous THF (5 mL) was treated at ambient temperature with phosphorus(V) sulfide (0.77 g). The mixture was heated at reflux under a nitrogen atmosphere for 2.5 hours. The reaction mixture was diluted with a large excess of saturated aqueous sodium carbonate solution (50 mL) and DCM (50 mL). The resulting mixture was stirred at ambient temperature for 20 minutes, the phases were separated, and the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude material was purified by preparative thin-layer chromatography (silica, 7% MeOH-DCM as eluent) to afford the product (235 mg) as a pale yellow solid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 2.5 hours
  3. customthe phases were separated
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by preparative thin-layer chromatography (silica, 7% MeOH-DCM as eluent)

출처 및 근거

ORD 기록
ord-9af4f55f8b57408da10838e543d28ed6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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