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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 636315Generated: October 26, 2026

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

https://huagongshe.com/reaction/636315

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-MethylmorpholineHCID 7972—
ReactantDicyclohexylcarbodiimideHCID 10868—
Reactant2-Anthraquinonecarboxylic acidHCID 67030—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantHCID 10555399HCID 10555399—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
Product6-(1-Anthraquinonecarbonyl)-3,10-bis (2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicylo[10.3.1]hexadeca-1(16),12,14-trieneHCID 2125733376%

Reaction Steps

The title compound was prepared following the procedures illustrated above in Example 75 using 3,10-bis (2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo-[10.3.1]hexadeca-1(16),12,14-triene (1.0 g, 1.7 mmol), anthraquinone-2-carboxylic acid (0.43 g, 1.7 mmol), DCC (0.35 g, 1.7 mmol), HOBT (0.23 g, 1.7 mmol) and 4-methylmorpholine (0.25 g, 2.5 mmol) in 10 mL of anhydrous THF and 20 mL of anhydrous DMF in 56 h. The compound was purified by flash chromatography on a silica gel column using 200:1 CH2Cl2—MeOH as an eluent to give 1.06 g (76%) of the title compound as a pale yellow foam.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06191273B1
Source datasetuspto-grants-2001_02
ORD IDord-45b22fedd8d549d0b0b74ce51cdd5c54
Source noteuspto-grants-2001_02