Tert-Butyl nitrite → 1-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513605Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamide (Intermediate 275) (1.3 g, 3.89 mmol) was dissolved in AcOH (13 ml) and the mixture was stirred at 0° C. for 5 min. The solution was cooled to −10° C. and t-butyl nitrite (0.7 ml, 5.83 mmol) was added dropwise and the mixture was stirred at room temperature 30 min. The mixture was quenched with sat. NaHCO3 solution and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (400 mg, 33%) after the purification by column chromatography with DCM/MeOH (90:10) as the eluent.

Workup

temperatureThe solution was cooled to −10° C.
stirringthe mixture was stirred at room temperature 30 min
customThe mixture was quenched with sat. NaHCO3 solution
extractionthe aqueous phase was extracted with EtOAc
washThe organic phase was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6ba6e3f86ae041d9b71cca0cde9eab77
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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