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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2414260Generated: November 2, 2026

Methanol → Methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate

https://huagongshe.com/reaction/2414260

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantDimethylformamideHCID 6228—
ReactantPotassium cyanateHCID 11378442—
ReactantMethyl 3-(bromomethyl)-4-chlorobenzoateHCID 12144656—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
ProductMethyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoateHCID 22645128—

Reaction Conditions

Temperature90 °C

Reaction Steps

16.0 g of the obtained methyl 3-bromomethyl-4-chlorobenzoate, 15.0 g of potassium cyanate and 35 ml of methanol were added to 200 ml of N,N-dimethylformamide, followed by stirring at 90° C. for 4 hours. After completion of the reaction, water was added to the reaction mixture, extraction with ethyl acetate was carried out, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropanol to obtain 25.2 g of methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate as white crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06812229B1
Source datasetuspto-grants-2004_11
ORD IDord-d4526409a12a456bb193fe73c51b7090
Source noteuspto-grants-2004_11