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

HRID 636317
Notes
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Reaction equation

HRID 636317 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0bb5170e162e468dbffe3a5ccdbf1189
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06191273B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes