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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 9720Generated: October 25, 2026

Methyl iodide → 6-Amino-4-methyl-2H-1,4-benzothiazin-3(4H)-one

https://huagongshe.com/reaction/9720

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantAmmonium ChlorideHCID 25517—
Reactant6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-oneHCID 686901—
SolventDimethylformamideHCID 6228—
Product6-Amino-4-methyl-2H-1,4-benzothiazin-3(4H)-oneHCID 2198814763.9%

Reaction Steps

4.5 g 6-Amino-4H-benzo[1,4]thiazin-3-one in 50 ml DMF was treated in portions with 0.695 g 95% sodium hydride at room temperature. After 30 min, 3.548 g methyl iodide were added dropwise at 0° C. and stirring was continued for another 30 min. The mixture was poured into ice and ammonium chloride solution and extracted with CH2Cl2. Chromatography on silica yielded 3.1 g crude product, which was further purified by trituration with diethyl ether.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07091345B2
Source datasetuspto-grants-2006_08
ORD IDord-ae7541c76b774e8fa0cc87517c966110
Source noteuspto-grants-2006_08