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

HRID 636318Notes

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:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>>[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:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 7969Thiophenol

HCID 11430Potassium Carbonate

HCID 212573336-(1-Anthraquinonecarbonyl)-3,10-bis (2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicylo[10.3.1]hexadeca-1(16),12,14-triene

Product 1

HCID 545331066-(1-Anthraquinonecarbonyl)-3,6,10,16-tetraazabicyclo-[10.3.1]hexadeca-1(16),12,14-trieneYield 80%

Procedure

The title compound was prepared following the procedures illustrated above in Example 78 using 6-(1-anthraquinonecarbonyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (1.02 g, 1.24 mmol), thiophenol (0.41 g, 3.72 mmol) and K2CO3 (1.7 g, 12.5 mmol). The crude material was purified by flash chromatography on a silica gel column using CH2Cl2 and then MeOH, 15:1 MeOH—NH4OH (30%) as eluents to give 0.45 g (80%) of the title compound as a pale yellow foam.

Workup

customThe title compound was prepared
customThe crude material was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record: ord-5934d6d71a1543e391f880063694f60b
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06191273B1

Reaction notes

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