Acetic Acid → 5H-6-Thia-1,4,5-triaza-chrysene 6,6-dioxide

HRID 513621Notes

Reaction equation

HRID 513621 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:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[CH:15][CH:16]=[N:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O.CC(O)=O>C1COCC1>[N:17]1[C:18]2[C:13](=[C:12]3[C:21](=[CH:20][CH:19]=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:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 681833572-Amino-N-quinoxalin-5-yl-benzenesulfonamide2×

Product 1

HCID 681833315H-6-Thia-1,4,5-triaza-chrysene 6,6-dioxideYield 16.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-quinoxalin-5-yl-benzenesulfonamide (Intermediate 304) (440 mg, 1.4 mmol), t-butyl nitrite (0.27 ml, 2.19 mmol), AcOH (4.5 ml) and THF (4.5 ml) gave the title compound (65 mg, 16%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-b04756c341914a48baf19d9980aa6e5e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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