Triphosgene → 2-(6-methoxy-5-methylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772880Notes

Reaction equation

HRID 1772880 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH3:20])=[C:16]([CH3:18])[CH:17]=1)(=[O:10])=[O:9].Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[CH3:20][O:19][C:15]1[N:14]=[CH:13][C:12]([N:11]2[C:22](=[O:24])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2(=[O:9])=[O:10])=[CH:17][C:16]=1[CH3:18]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 900307172-amino-N-(6-methoxy-5-methylpyridin-3-yl)benzenesulfonamide

Product 1

HCID 900551072-(6-methoxy-5-methylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideYield 385.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from 2-amino-N-(6-methoxy-5-methylpyridin-3-yl)benzenesulfonamide (2.60 g) and triphosgene (815 mg, 2.75 mmol) in anhydrous 1,4-dioxane (160 mL) using the methods of (IntA1) step 3. Concentration in vacuo after completion of the reaction yielded the title compound (3.38 g, 10.6 mmol, approximately 80% purity by LCMS) which was used without further purification.

Workup

  1. concentrationConcentration in vacuo after completion of the reaction

Sources & evidence

ORD record
ord-1b0846a78d594e4793732f7266de78a1
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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