[CH3:1][C:2]1[C:6]2[C:7](=O)[CH2:8][CH:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:5]=2[O:4][CH:3]=1.[C:17]([NH:20][NH2:21])([NH2:19])=[NH:18].[ClH:22].Cl.O>C(O)C>[ClH:22].[NH:20]([N:21]=[C:7]1[C:6]2[C:2]([CH3:1])=[CH:3][O:4][C:5]=2[CH2:10][CH:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH2:8]1)[C:17]([NH2:19])=[NH:18]A mixture of 3-methyl-6-(2-thienyl)-4,5,6,7-tetrahydrobenzofuran-4-one (0.30 g), aminoguanidine hydrochloride (0.15 g), concentrated hydrochloric acid (0.065 ml), water (0.065 ml) and ethanol (30 ml) was refluxed for 2.5 hours. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethanol to give 4-guanidinoimino-3-methyl-6-(2-thienyl)-4,5,6,7-tetrahydrobenzofuran hydrochloride (Compound 48) (0.36 g) as colorless crystals.
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