Pyridine → 2-(2,6-Dimethoxypyridin-4-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772866Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-])=O.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([NH2:22])[CH:19]=[C:18]([O:23][CH3:24])[N:17]=1.N1C=CC=CC=1.[O:31]1CCOC[CH2:32]1>>[CH3:24][O:23][C:18]1[CH:19]=[C:20]([N:22]2[C:32](=[O:31])[NH:1][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:10]2(=[O:12])=[O:11])[CH:21]=[C:16]([O:15][CH3:14])[N:17]=1

Participants

Reactant 4

HCID 1049Pyridine

HCID 155402-Nitrobenzenesulfonyl chloride

HCID 312751,4-Dioxane

HCID 222201912,6-Dimethoxypyridin-4-amine

Product 1

HCID 900551152-(2,6-Dimethoxypyridin-4-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Procedure

The title compound (0.40 g, 1.19 mmol) was prepared in three steps from 2-nitrobenzenesulfonyl chloride (2.66 g, 12.0 mmol), 2,6-dimethoxypyridin-4-amine (2.04 g, 13.2 mmol) and pyridine (2.9 mL, 36.0 mmol) in 1,4-dioxane (48 mL) using the methods of (IntA19).

Sources & evidence

ORD record: ord-1a3799a77045462abb5d93ef8d3af31a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249160B2

Reaction notes

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