Lawesson's reagent → 2-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indole

HRID 1515268ノート

反応式

HRID 1515268 の反応式
Cl[CH2:2][CH2:3][NH:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>ClC(Cl)C.C1(C)C=CC=CC=1>[S:28]1[CH2:2][CH2:3][N:4]=[C:5]1[C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17]

参加物

5

反応物 2

HCID 87949Lawesson's reagentHCID 866443587-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide

生成物 1

HCID 579015982-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indole収率 60%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

7-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide (267 mg, 1 mmol) prepared in Step B was dissolved in dichloroethane (10 mL) and toluene (10 mL), and Lawesson's Reagent (1.29 g, 3.2 mmol) was added thereto. The mixture was refluxed for 4 h, and distilled under reduced pressure. Water was added thereto, and the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and the concentrate was purified by column chromatography to give the title compound as a product of the cyclization reaction (148 mg, Yield 60%).

後処理

  1. temperatureThe mixture was refluxed for 4 h
  2. distillationdistilled under reduced pressure
  3. additionWater was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customthe concentrate was purified by column chromatography

出典と根拠

ORDレコード
ord-c9b1310144d74e7a917bd898cc4d886b
出典データセット
uspto-grants-2012_07
特許番号
US08222414B2

反応ノート

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