Bromine → N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methylphenyl}-3-(1-cyanocyclopropyl)benzamide

Reaction equation

[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH:14][C:15](=[O:27])[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4([C:25]#[N:26])[CH2:24][CH2:23]4)[CH:17]=3)[CH:10]=[CH:11][C:12]=2[CH3:13])=[CH:4][CH:3]=1.[S-:30][C:31]#[N:32].[K+].BrBr>>[NH2:32][C:31]1[S:30][C:3]2[CH:4]=[C:5]([O:6][C:7]3[CH:8]=[C:9]([NH:14][C:15](=[O:27])[C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]5([C:25]#[N:26])[CH2:24][CH2:23]5)[CH:17]=4)[CH:10]=[CH:11][C:12]=3[CH3:13])[CH:28]=[CH:29][C:2]=2[N:1]=1

Participants

Reactant 3

HCID 24408Bromine

HCID 516872Potassium thiocyanate

HCID 67312970N-[3-(4-aminophenoxy)-4-methylphenyl]-3-(1-cyanocyclopropyl)benzamide

Product 1

HCID 86655387N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methylphenyl}-3-(1-cyanocyclopropyl)benzamideYield 20%

Procedure

Using N-[3-(4-aminophenoxy)-4-methylphenyl]-3-(1-cyanocyclopropyl)benzamide (1.92 g, 5.0 mmol), potassium thiocyanate (1.94 g, 20.0 mmol) and bromine (1.20 g, 7.50 mmol), and in the same manner as in Example A25(v), the title compound (0.44 g, 20%) was obtained as a pale-yellow powder. 1H-NMR (CDCl3, 300 MHz) δ 1.50 (2H, dd, J=5.1, 7.8 Hz), 1.76 (2H, dd, J=5.1, 7.8 Hz), 2.25 (3H, s), 6.50 (2H, br s), 6.98-7.04 (2H, m), 7.21-7.25 (2H, m), 7.41-7.65 (4H, m), 7.71-7.85 (3H, m).