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

HRID 513609Notes

Reaction equation

HRID 513609 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[C:22]([F:25])([F:24])[F:23])(=[O:10])=[O:9].N(OC(C)(C)C)=O>CC(O)=O>[F:25][C:22]([F:24])([F:23])[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:9])(=[O:10])[NH:11]3)[N:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 681834872-Amino-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 601643091-Trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 20.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a similar fashion using route 16 general procedure 61, 2-amino-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 279) (300 mg, 0.82 mmol), t-butyl nitrite (0.14 ml, 1.22 mmol) and AcOH (4 ml) gave the title compound (60 mg, 16%) after purification by column chromatography with DCM/MeOH: aq.NH3 (99:1:2 drops) as the eluent.

Sources & evidence

ORD record
ord-4732581720054db39728949f48095e40
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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