Triethylamine → HCID 70452962, compound

Participants

Reaction Steps

A solution of triethylamine (1.52 g, 0.0150 mole) in 5 ml methylene chloride was added to a stirred solution of 5-bromo-2,4-dimethoxybenzoic acid (3.92 g, 0.0150 mole) in 75 ml of methylene chloride. After stirring for 20 minutes at room temperature, the mixture was cooled to 0° C. with an ice water bath. A solution of ethyl chloroformate (1.63 g, 0.0150 mole) in 10 ml methylene chloride was added dropwise to the cold stirred reaction mixture, and the mixture stirred at 0° C. for 30 minutes. Then a solution of 4-amino-1,2-diethylpyrazolidine (2.15 g, 0.0150 mole) in 10 ml of methylene chloride was added dropwise to the cold reaction mixture. The mixture was stirred for 30 minutes at 0° C. and then allowed to warm to room temperature and stirred for 16 hr. The mixture was concentrated to a semi-solid residue which was triturated in 10 ml methanol and 20 ml of a saturated aqueous sodium bicarbonate solution. The mixture was extracted with 2×75 ml portions of methylene chloride, the extract dried (magnesium sulfate) and concentrated to give a solid. The solid was triturated with isopropyl ether and filtered to give 4.28 g (73.9%) of cream-colored solid; recrystallization from isopropyl ether gave 2.04 g of the product; m.p. 113.5°-114.5° C. NMR analysis showed the solid to be a monohydrate, vacuum drying at 54° C. for 16 hrs gave the hemihydrate, m.p. 114°-115° C.

Provenance & Evidence