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

HRID 513597Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[CH:17]2)(=[O:10])=[O:9].C(ON=O)(C)(C)C>C(O)(=O)C>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]2[C:21]([N:20]=1)=[C:12]1[C:13]([C:4]3[C:3]([S:8](=[O:10])(=[O:9])[NH:11]1)=[CH:2][CH:7]=[CH:6][CH:5]=3)=[CH:14][CH:15]=2

Participants

Conditions

Temperature: 10 °C

Procedure

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%).

Workup

temperaturethe reaction was slowly warmed to room temperature over 1 h
customThe reaction was then quenched with water (4 ml)
concentrationthe resulting solution was concentrated in vacuo
customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record: ord-b30dafd11cc6483bb1736c3326b9b700
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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