Methylamine → 3-[2-(ethylthio)phenyl]-4-methyl-5-(4-pentylphenyl)-4H-1,2,4-triazole

反応式

[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1O[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=2)=[N:13][N:14]=1)[CH3:2].FC(F)(F)C([O-])=O.[CH3:33][NH3+:34].CN>>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:34]([CH3:33])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=2)=[N:13][N:14]=1)[CH3:2]

参加物

反応物 3

HCID 6329Methylamine

HCID 15260452Methylammonium trifluoroacetate

HCID 59532610HCID 59532610、化合物

生成物 1

HCID 595326063-[2-(ethylthio)phenyl]-4-methyl-5-(4-pentylphenyl)-4H-1,2,4-triazole

実験手順

2-[2-(Ethylthio)phenyl]-5-(4-pentylphenyl)-1,3,4-oxadiazole (1-E) (100 mg, 0.28 mmol), methylammonium trifluoroacetate (1.64 g, 11.34 mmol, prepared by combining equal amounts of methylamine and trifluoroacetic acid in ether followed by evaporation in vacuo) and methylamine (2M/MeOH, 5.68 mL, 11.34 mmol) were stirred together in a glass bomb at 150° C. for 2.5 d. The mixture was evaporated in vacuo and the residue partitioned between methylene chloride and water. The organic phase was washed with water, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative TLC (silica gel, ethyl acetate:hexane, 7:3) to provide 3-[2-(ethylthio)phenyl]-4-methyl-5-(4-pentylphenyl)-4H-1,2,4-triazole (1-F). MS m/z 366 (M+1). 1H NMR (500 MHz, CDCl3): δ 0.96 (t, 3H); 1.29 (t, 3H); 1.40 (m, 4H); 1.73, (m, 2H); 2.73, (t, 2H); 2.90 (q, 2H); 3.58 (s, 3H); 7.37 (m, 3H); 7.55 (m, 3H); 7.72, (d, 2H).