Triethylamine → HCID 19854909, compound

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=2)[CH:5]=[C:4]([CH3:17])[C:3]=1[NH:18][C:19]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])=S.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>C(#N)C>[CH3:17][C:4]1[CH:5]=[C:6]([O:8][C:9]2[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=2)[CH:7]=[C:2]([CH3:1])[C:3]=1[N:18]=[C:19]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

Procedure

A reaction vessel is charged with 16.6 g of N-[2,6-dimethyl-4-(3,5-dichloro-2-pyridyloxy)phenyl]-N'-tert-butylthiourea and 12.8 g of 2-chloro-1-methylpyridinium iodide in 150 ml of acetonitrile. With stirring, a solution of 8.4 g of triethylamine in 80 ml of acetonitrile is added dropwise at room temperature. The reaction mixture is subsequently stirred for 2 hours at 80° C. and then concetrated by rotary evaporation at 50° C. 150 ml of hexane are added to the residue and the resultant solution is filtered. The hexane phase is washed with three 30 ml portions of cold water, dried over sodium sulfate and filtered. The filtrate is concentrated by evaporation, affording the title compound of the formula ##STR5## as a clear pale yellow oil which crystallises on standing and has a melting point of 69°-71° C. (compound 1).