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

HRID 1458871
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HRID 1458871 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 220970767-Amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione

생성물 1

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

시약·촉매·용매 1

HCID 21735183Dimethylformamide toluene
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-943720297c4f4a73a3edce4ed2607d99
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05852017

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