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

HRID 79457ノート

反応式

HRID 79457 の反応式
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

参加物

6

反応物 5

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9af4f55f8b57408da10838e543d28ed6
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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