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Thiophenol → 6-(1-Pyrenebutyryl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-triene

HRID 636317
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HRID 636317 반응식
[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([N:22]2[CH2:36][CH2:35][CH2:34][N:33](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:32][C:31]3[N:49]=[C:27]([CH:28]=[CH:29][CH:30]=3)[CH2:26][N:25](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:24][CH2:23]2)=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([N:22]2[CH2:36][CH2:35][CH2:34][NH:33][CH2:32][C:31]3[N:49]=[C:27]([CH:28]=[CH:29][CH:30]=3)[CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 107242806-(1-Pyrenebutyryl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene

생성물 1

HCID 105530946-(1-Pyrenebutyryl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-triene수율 87.8%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A mixture of 6-(1-Pyrenebutyryl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-triene (2.26 g, 2.6 mmol), thiphenol (0.87 g, 7.8 mmol) and K2CO3 (3.22 g, 23.4 mmol) in 20 mL of DMF was stirred at rt overnight. The solvent was evaporated and the residue was dissolved in CHCl3—H2O. The organic phase was separated and the aqueous phase was extracted with CHCl3. The combined organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on a silica gel column using CH2Cl2 and then 3:1 CH2Cl2—MeOH as eluents to give 1.12 g (65%) of the title compound as a white foam.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in CHCl3—H2O
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with CHCl3
  5. dry with materialThe combined organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-0bb5170e162e468dbffe3a5ccdbf1189
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06191273B1

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