Water → HCID 178488949, compound

Reaction equation

[C:1](OCC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:10][O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[NH:17])=[CH:14][CH:13]=1.O>C(Cl)(Cl)Cl>[OH:6][C:1]1[N:18]=[C:16]([C:15]2[CH:19]=[CH:20][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[N:17]=[C:3]([CH3:5])[CH:2]=1

Participants

Procedure

Under N2, a solution of ethyl acetoacetate (7.15 g, 0.053 mol) in CHCl3 (200 ml) was added dropwise to a suspension of 4-methoxybenzamidine in CHCl3 (200 ml). After stirring at room temperature overnight, water was added to the solution. The aqueous phase was separated and extracted with CHCl3 and the organic layers were combined, dried (Na2SO4), filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product was eluted with 2% CH3OH--CHCl3 to yield 8.58 g (75%) of product, m.p. 198°-199° C.