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Triphenylphosphine Oxide → 2-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indole

HRID 1851394
ノート
印刷プレビュー

反応式

HRID 1851394 の反応式
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[N+:36]([C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:47]=1[NH:46][C:45]([C:48]([NH:50][CH2:51][CH2:52][S:53]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:44]2)([O-:38])=[O:37]>ClCCl>[S:53]1[CH2:52][CH2:51][N:50]=[C:48]1[C:45]1[NH:46][C:47]2[C:43]([CH:44]=1)=[CH:42][CH:41]=[CH:40][C:39]=2[N+:36]([O-:38])=[O:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 579017857-Nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

生成物 1

HCID 579015982-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indole収率 81.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of triphenylphosphine oxide (16.7 g) in dichloromethane (30 mL) was slowly added trifluoromethanesulfonic anhydride (5.0 mL) at 0° C., and the mixture was stirred for 10 min and 7-nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (10.1 g) was added. The reaction mixture was stirred at room temperature for 8 hr and concentrated. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (4.0 g, yield 81%) as yellow crystals.

後処理

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at room temperature for 8 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-be26b043efe54646857063c24c75e3d6
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08957070B2

反応ノート

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