Acetic Acid → 3,9-Dichloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513616Notes

Reaction equation

HRID 513616 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]=[C:20]([Cl:23])[CH:19]=[CH:18]2)(=[O:11])=[O:10].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]2[C:22]([N:21]=1)=[C:13]1[C:14]([C:4]3[C:3]([S:9](=[O:11])(=[O:10])[NH:12]1)=[CH:2][CH:7]=[C:6]([Cl:8])[CH:5]=3)=[CH:15][CH:16]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 86669762HCID 86669762, compound2×

Product 1

HCID 601645443,9-Dichloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-4-chloro-N-(2-chloro-quinolin-8-yl)-benzenesulfonamide (Intermediate 287) (0.1 g, 0.27 mmol), t-butyl nitrite (0.05 ml, 0.41 mmol) and AcOH:THF (1 ml: 2 ml), gave the title compound (0.04 g, 45%) after purification by column chromatography with DCM/MeOH (90:10) as the eluent.

Sources & evidence

ORD record
ord-44a8e2d55aac455bbd558f96d902b85e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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