Hydrochloric Acid → HCID 16734139, compound

Participants

Reaction Conditions

Reaction Steps

199 mg (0.6 mmol) of 3-(3-aminobenzyl)-5-(4-chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one are dissolved in 4 ml of THF in an 8 ml multi-stirrer vessel, 107 μl of diisopropylethylamine are added, the mixture is cooled in an ice/water bath, 78 μl of isopropylidene chloroformate are added dropwise, and the mixture is subsequently stirred at 70° C. for 1 h. The mixture is subsequently cooled to room temperature, and 107 μl (0.72 mmol) of 3-diethylaminopropan-1-ol is added, and the mixture is refluxed for 96 h. For work-up, the reaction mixture is diluted with 30 ml of dichloromethane, shaken with 20 ml of 1 N HCl and 20 ml of 2 N NaOH, dried over sodium sulfate, evaporated to dryness and purified by chromatography (dichloromethane/methanol: 9:1). The combined fractions containing the product are evaporated to dryness and crystallised from diethyl ether/petroleum ether 40-60, giving 128 mg of 3-diethylaminopropyl {3-[5-(4-chlorophenyl)-3,6-dihydro-2-oxo-6H-1,3,4-thiadiazin-3-ylmethyl]phenyl}carbamate (“A1”), m.p. 115-117°;

Provenance & Evidence