1,1'-Carbonyldiimidazole → 2-(5,6-dimethylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772882Notes

Reaction equation

HRID 1772882 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]([CH3:19])=[C:16]([CH3:18])[CH:17]=1)(=[O:10])=[O:9].[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>ClCCCl>[CH3:18][C:16]1[CH:17]=[C:12]([N:11]2[C:20](=[O:21])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2(=[O:10])=[O:9])[CH:13]=[N:14][C:15]=1[CH3:19]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 900306042-amino-N-(5,6-dimethylpyridin-3-yl)benzenesulfonamide

Product 1

HCID 900551232-(5,6-dimethylpyridin-3-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideYield 55%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound (2.17 g, 7.15 mmol) was prepared from 2-amino-N-(5,6-dimethylpyridin-3-yl)benzenesulfonamide (2.7 g, 13.0 mmol) and 1,1′-carbonyldiimidazole (4.74 g, 29.2 mmol) in 1,2-dichloroethane (25 mL) at 110° C. for 3 h using the methods of (IntA14), step 3.

Sources & evidence

ORD record
ord-95ade9df5a2047db95f860e5777f1ee8
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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