Stannous chloride dihydrate → HCID 118324121, compound

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>CO.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

Procedure

A solution of 2-((4-chlorophenyl)(4-nitrophenyl)methyl)thiazole (550 mg, 1.663 mmol, 1 equip) and tin(II) chloride dihydrate (2.321 g, 9.976 mmol, 6 equip) in MeOH (11 mL) and concentrated HCl (1 ml) was heated at reflux temperature until analytical HPLC showed conversion to the desired product. The reaction mixture was made basic with excess triethylamine. The resulting thick precipitate was filtered through CELITE and the filter pad washed thoroughly with methanol. The filtrate was concentrated and the residue was purified by MPLC using ethyl acetate-heptane as the eluent to yield 4-((4-chlorophenyl)(thiazol-2-yl)methyl)aniline as a white solid (250 mg, 50%). (ES, m/z) 301, 303 [M+H]+