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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 49154Generated: October 26, 2026

Methylamine → 4-(4-hydroxy-phenoxy)-N-methyl-benzamide

https://huagongshe.com/reaction/49154

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
ReactantMethyl chloroformateHCID 6586—
ReactantTriethylamineHCID 8471—
Reactant4-(4-Hydroxy-phenoxy)-benzoic acidHCID 615542—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product4-(4-hydroxy-phenoxy)-N-methyl-benzamideHCID 18184026—

Reaction Steps

To a mixture of 4-(4-Hydroxy-phenoxy)-benzoic acid (0.25 g, 1.09 mmol), triethylamine (0.15 mL, 1.07 mmol) and tetrahydrofuran (THF) (5.0 mL) at 0° C. was added methylchloroformate (0.084 mL, 0.10 g, 1.1 mmol). After stirring for 15 minutes, excess methylamine was added via a sparge tube, and stirring was continued for 10 minutes. The mixture was diluted with water, extracted three times with ethyl acetate, and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo, affording 1 4-(4-Hydroxy-phenoxy)-N-methyl-benzamide as a colorless syrup.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06706723B2
Source datasetuspto-grants-2004_03
ORD IDord-6ab78729e17448358004cb22c51c592f
Source noteuspto-grants-2004_03