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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 513615Generated: October 30, 2026

Acetic Acid → 9-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carbonitrile

https://huagongshe.com/reaction/513615

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantTert-Butyl nitriteHCID 10906—
Reactant2-Amino-4-chloro-N-(5-cyano-quinolin-8-yl)-benzenesulfonamideHCID 68183279—
SolventTetrahydrofuranHCID 8028—
Product9-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysene-12-carbonitrileHCID 6016443843.3%

Reaction Steps

In a similar fashion using route 16 general procedure 61, 2-amino-4-chloro-N-(5-cyano-quinolin-8-yl)-benzenesulfonamide (Intermediate 286) (100 mg, 0.27 mmol), t-butyl nitrite (0.047 ml, 0.41 mmol) and AcOH: THF (2 ml: 1 ml) gave the title compound (40 mg, 42%) after purification by column chromatography with chloroform/MeOH (99.5:0.5) as the eluent.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09102688B2
Source datasetuspto-grants-2015_08
ORD IDord-7a0a29bd41a14cbfb4e9dd5b5a267f4a
Source noteuspto-grants-2015_08