2,6-Dichlorophenoxyacetic acid → HCID 18603263, compound

Participants

Reaction Steps

2,6-dichlorophenoxyacetic acid (0.50 g, 2.3 mmol) was treated with thionyl chloride (6 ml) at room temperature for 60 hours. The solution was concentrated in vacuo to give an oil which was dissolved in dichloromethane (2.5 ml) and added dropwise over three mi-nutes to a stirred solution of trans-(±)-N, N'-dimethylcyclohexane-1,2-diamine (0.35 g, 3.1 mmol) in dichloromethane (2.5 ml). After 1.5 hours at room temperature the mixture was filtered and the filtrate treated with diethyl ether until precipitation occurred. The resulting white solid was recrystallized (dichloromethane-diethyl ether) to give trans-(±)-2-(2,6-dichlorophenoxy)-N-methyl-N-[2-(methylamino)cyclohexyl]acetamide monohydrochloride (171 mg, 19%); VmaxC=0 (liquid file) 1655 cm-1.

Provenance & Evidence