Ethylenediamine → Agn-PC-0niccc
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]#[N:12])=[N:2]1.[CH2:13](N)[CH2:14][NH2:15].C(=S)=S.C(Cl)(Cl)[Cl:21]>>[ClH:21].[NH:12]1[CH2:13][CH2:14][N:15]=[C:11]1[CH2:10][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][N:2]=1Participants
5
Procedure
A mixture of 1,2-benzisoxazole-3-acetonitrile (1.6 g), ethylenediamine (0.7 g) and carbon disulfide (0.2 ml) was heated at 130° to 150°C for 0.5 hour and then allowed to stand at room temperature overnight. to the reaction mixture was added chloroform and the insoluble substance was filtered off. The filtrate was subjected to silica gel column chromatography and eluted with 10 to 20 % methanol-chloroform. The eluates were collected and treated with ethanolic hydrochloric acid to give the hydrochloride. The product was treated with charcoal and then recrystallized from ethanol to give the desired compound (0.4 g). m.p. 223° to 228°C.