Water → HCID 68085473, compound

Participants

Reaction Conditions

Reaction Steps

4.87 g (0.03 mol) of 3-methylcinammic acid, 49 ml of toluene and 0.19 g (2.6 mmol) of N,N-dimethylormamide are provided and mixed with 4.3 g (0.036 mol) of thionyl chloride. Stirring takes place for 1 hour followed by heating to 60° C. The toluene and excess thionyl chloride are drawn off under vacuum. Then 24 ml of toluene and 4.3 g (0.033 mol) of ethyldiisopropylamine are added at 60° C. A solution of 5.8 g (0.033 mol) of cyclohexyl-2-pyridinylamine (for preparation see E. H. Mørkved, Journal f. prakt.Chemie, 1986, 328 (3), 401-406) in toluene is added and stirred for 2 hours at 60-65° C. Hydrolysis with water is performed and the organic phase is washed with water, 1 N NaOH and again with water. The organic phase is rotated and the residue crystallised from MTBE. The crystallised solid is drawn off, washed with MTBE and dried, wherein the desired compound is obtained.

Provenance & Evidence