Pyridine → 2-(5,6-Dimethoxypyridin-2-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772865Notes

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:17]=[CH:18][C:19]([NH2:24])=[N:20][C:21]=1[O:22][CH3:23].N1C=CC=CC=1.[O:31]1CCOC[CH2:32]1>>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([N:24]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])=[N:20][C:21]=1[O:22][CH3:23]

Participants

Reactant 4

HCID 1049Pyridine

HCID 155402-Nitrobenzenesulfonyl chloride

HCID 312751,4-Dioxane

HCID 467391485,6-Dimethoxypyridin-2-amine

Product 1

HCID 900548642-(5,6-Dimethoxypyridin-2-yl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Procedure

The title compound (0.30 g, 0.89 mmol) was prepared in three steps from 2-nitrobenzenesulfonyl chloride (1.05 g, 4.72 mmol), 5,6-dimethoxypyridin-2-amine (0.80 g, 5.19 mmol) and pyridine (1.15 mL, 14.2 mmol) in 1,4-dioxane (19 mL) using the methods of (IntA19).

Sources & evidence

ORD record: ord-e15b432c0eb249e08e06c8d89e15a0ea
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249160B2

Reaction notes

Loading…