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

HRID 636319Notes

Reaction equation

HRID 636319 reaction equation
[C:1]1([C:17]([N:19]2[CH2:33][CH2:32][CH2:31][N:30](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:29][C:28]3[N:46]=[C:24]([CH:25]=[CH:26][CH:27]=3)[CH2:23][N:22](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:21][CH2:20]2)=[O:18])[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:67].[K+].[K+]>CN(C=O)C>[CH3:17][OH:18].[NH4+:19].[OH-:67].[C:1]1([C:17]([N:19]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][C:28]3[N:46]=[C:24]([CH:25]=[CH:26][CH:27]=3)[CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[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

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 108192156-(1-Pyrenecarbonyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene

Product 2

HCID 108371856-(1-Pyrenecarbonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-trieneYield 154.3%HCID 21894508Ammonium hydroxide methanolYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared following the procedures illustrated above in Example 78 using 6-(1-pyrenecarbonyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (0.64 g, 0.78 mmol), thiophenol (0.26 g, 2.34 mmol) and K2CO3 (1.0 g, 7.4 mmol) in 20 mL of DMF. The product was purified by flash chromatography on a silica gel column using 10:1 CH2Cl2—MeOH and then 10:1 MeOH—NH4OH (30%) to give 0.27 g (77%) of the title compound as a pale yellow foam.

Workup

  1. customThe title compound was prepared
  2. customThe product was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-6b92337c7a484d1f82778d345c1b7caa
Source dataset
uspto-grants-2001_02
Patent number
US06191273B1

Reaction notes

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