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p-Toluenesulfonic acid → 1-Cyclohexyl-6-(3-formyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione

HRID 861533
ノート
印刷プレビュー

反応式

HRID 861533 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:18])[N:9]2C2CCCCC2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[CH:23]([CH:25]1[CH2:29][CH:28](OC)O[CH:26]1OC)=[O:24].[C:34]1(C)[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH:34]1([N:6]2[C:5]3[C:10](=[CH:11][C:2]([N:1]4[CH:28]=[CH:29][C:25]([CH:23]=[O:24])=[CH:26]4)=[C:3]([N+:20]([O-:22])=[O:21])[CH:4]=3)[NH:9][C:8](=[O:18])[C:7]2=[O:19])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1
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 6101p-Toluenesulfonic acidHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 220970767-Amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione

生成物 1

HCID 220972041-Cyclohexyl-6-(3-formyl-1-pyrrolyl)-7-nitro-2,3(1H,4H)-quinoxalinedione収率 22%

試薬・触媒・溶媒 1

HCID 21735183Dimethylformamide toluene
溶媒

実験手順

4 g (13 mmol) of the product 37b, 2.3 g (14 mmol) of 3-formyl-2,5-dimethoxytetrahydrofuran and a spatula tip of 4-toluenesulfonic acid in 200 ml of dimethylformamide/toluene (1:1) were refluxed with a water trap. After the reaction was complete (TLC check), the mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated under reduced pressure. This residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=40/20/1) to yield 1.1 g (22%) of the product.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customThis residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/glacial acetic acid=40/20/1)

出典と根拠

ORDレコード
ord-f46f7893d50f46868cd06b6fe822a852
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05714489

反応ノート

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