2-Aminopyridine-3-sulfonamide → 2H-Pyrido(2,3-e)-1,2,4-thiadiazine, 1,1-dioxide

Reaction equation

[NH2:1][C:2]1[C:7]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:12]([O-])([O-])OCC>>[S:8]1(=[O:9])(=[O:10])[C:7]2[CH:6]=[CH:5][CH:4]=[N:3][C:2]=2[NH:1][CH:12]=[N:11]1

Participants

Reactant 2

HCID 17138682-Aminopyridine-3-sulfonamide

HCID 53630039Ethylorthoformate

Product 1

HCID 30540122H-Pyrido(2,3-e)-1,2,4-thiadiazine, 1,1-dioxide

Procedure

A mixture of 2 g of 2-aminopyridine-3-sulfonamide (Preparation 6) and 20 cm3 of ethyl orthoformate is brought to reflux for 1 hour. After cooling, the crystalline precipitate obtained is collected on a filter and washed with ether.

Workup

temperatureto reflux for 1 hour
temperatureAfter cooling
customthe crystalline precipitate obtained
customis collected on
filtrationa filter
washwashed with ether

Sources & evidence

ORD record: ord-df4f45697ba344a8a960a60e28988795
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05459138

Reaction notes

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