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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1470711Generated: November 2, 2026

Dimethyl Sulfate → Benzoic acid, 2-amino-3-chloro-, methyl ester

https://huagongshe.com/reaction/1470711

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfateHCID 6497—
ReactantPotassium CarbonateHCID 11430—
Reactant2-Amino-3-chlorobenzoic acidHCID 80807—
CatalystTetrabutylammonium BromideHCID 74236—
SolventTolueneHCID 1140—
ProductBenzoic acid, 2-amino-3-chloro-, methyl esterHCID 1103051196%

Reaction Conditions

Temperature80 °C

Reaction Steps

5.13 g (0.03 mol) of 2-amino-3-chlorobenzoic acid, ml of toluene, 0.97 g (0.003 mol) of tetrabutylammonium bromide, and 4.54 g (0.04 mol) of dimethyl sulfate were added to a 100 ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer, and a dropping funnel, and a mixture of 4.56 g (0.033 mol) of potassium carbonate and 9 ml of toluene was added dropwise with stirring at 80° C. Then, the mixture was stirred at 80° C. for 1 hour. The solution was analyzed by HPLC by the absolute calibration method, and as a result, the yield was 96%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006477B2
Source datasetuspto-grants-2015_04
ORD IDord-f12928dbd62846498c176d9ec347d926
Source noteuspto-grants-2015_04