Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 840369Generated: October 31, 2026

Sodium Bicarbonate → 6-(2-Thienyl)-2-methyl-1,4-benzoxazin-3-(4h)-one

https://huagongshe.com/reaction/840369

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
Reactant2-Thiopheneboronic acidHCID 2733960—
Reactant6-bromo-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 22622903—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
Product6-(2-Thienyl)-2-methyl-1,4-benzoxazin-3-(4h)-oneHCID 2262291933%

Reaction Conditions

Temperature100 °C

Reaction Steps

315 mg of 6-bromo-2-methyl-1,4-benzoxazin-3-(4H)-one is mixed in 4 ml of DME with 0.2 g of 2-thiopheneboronic acid and 150 mg of tetrakis-triphenylphosphine-palladium (O) and 340 mg of sodium bicarbonate (dissolved in 4 ml of water). It is stirred for some time at 100° C. The product is diluted with ethyl acetate, extracted 3 times with water, and dried with magnesium sulfate. It is concentrated by evaporation. The crude product is purified by column chromatography with a hexane/ethyl acetate mixture and yields pure 33% product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06365736B1
Source datasetuspto-grants-2002_04
ORD IDord-32bf2a6a5f0846fb80338bb81efe33f4
Source noteuspto-grants-2002_04