Acetic Acid → 9-chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513624Notes

Reaction equation

HRID 513624 reaction equation
N[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)(=[O:11])=[O:10].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[Cl:8][C:6]1[CH:5]=[C:4]2[C:3]([S:9](=[O:11])(=[O:10])[NH:12][C:13]3[C:14]2=[CH:15][CH:16]=[C:17]2[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]2)=[CH:2][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 167599552-Amino-4-chloro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 167599339-chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the similar fashion using route 16 general procedure 61, using 2-amino-4-chloro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 292) (150 mg, 0.45 mmol), t-butyl nitrite (0.08 ml, 0.67 mmol), AcOH (1.5 ml) and THF (1.5 ml) gave the title compound (20 mg, 14%) after purification by column chromatography with DCM/MeOH (99.7:0.3) as the eluent.

Sources & evidence

ORD record
ord-4f8cb15e94f549f7a5190137da19d432
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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