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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 513597Generated: October 31, 2026

Tert-Butyl nitrite → 3-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

https://huagongshe.com/reaction/513597

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTert-Butyl nitriteHCID 10906—
Reactant2-Amino-N-(2-methyl-quinolin-8-yl)-benzenesulfonamideHCID 16759519—
SolventAcetic AcidHCID 176—
Product3-Methyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideHCID 167595205%

Reaction Conditions

Temperature10 °C

Reaction Steps

2-Amino-N-(2-methyl-quinolin-8-yl)-benzenesulfonamide (Example Compound 15) (164 mg, 0.52 mmol) was suspended in acetic acid (3 ml) and cooled to 10° C. Tert-butylnitrite (93 μl, 0.79 mmol) was added and the reaction was slowly warmed to room temperature over 1 h. The reaction was then quenched with water (4 ml) and the resulting solution was concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (7 mg, 5%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09102688B2
Source datasetuspto-grants-2015_08
ORD IDord-b30dafd11cc6483bb1736c3326b9b700
Source noteuspto-grants-2015_08