Methyl isothiocyanate → 1-methyl-3-(3-quinoxalin-2-ylphenyl)thiourea
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[CH3:18][N:19]=[C:20]=[S:21]>C1(C)C=CC=CC=1>[CH3:18][NH:19][C:20]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[S:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 10 mmol) in hot toluene (80 mL), methyl isothiocyanate (0.73 g, 10 mmol) was added and the reaction mixture was heated overnight at reflux. The mixture was cooled to room temperature, the resulting precipitate was filtered to afford 1-methyl-3-[3-(quinoxalin-2-yl)phenyl]thiourea (2.0 g, 68% yield). LCMS calculated for C16H14N4S (M+H): 295.38. found 295. 1H-NMR (DMSO-d6, 250 Mhz) δH: 9.85 (1H, br. s), 9.55 (1H, s), 8.40-8.30 (1H, m), 8.20-8.00 (3H, m), 7.98-7.80 (3H, m), 7.70-7.60 (1H, m), 7.60-7.45 (1H, m).