Ethanol → HCID 23471640, compound

Participants

Reaction Steps

A mixture of 1-(3-chlorophenyl)piperazine (13 g, described in Example 11) and methylthiomethanimidamide hydrobromide (12.2 g) in ethanol (50 ml) was refluxed for 14 hr and evaporated. To the residue, 1N sodium ethoxide in ethanol (66 ml) and 2-methoxy-2,4,6-cycloheptatrien-1-one(9 g) were added. The mixture was refluxed for 2 hr and evaporated. The residue was chromatographed through a column of silica gel using ethyl acetate and the eluates were evaporated. The residue was crystallized from ethyl acetate to obtain the title compound (5.9 g): mp 217°-219° C; ir(mull)1615, 1590, 1575 and 1530 cm-1 ; uv max (MeOH) 289(ε9.870), 261(ε43,230) and 240 nm(ε29,040); nmr(CDCl3) δ 3.33(4H,t), 4.18(4H,t) and 7.5(9H,m) and Anal. Calcd for C18H17N4Cl: C, 66.56% H, 5.27% N, 17.25% and Found: C, 66.11% H, 5.10% N, 16.99%.

Provenance & Evidence