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

HRID 2190445Notes

Reaction equation

HRID 2190445 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

4

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 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).

Sources & evidence

ORD record
ord-b8e7169ee590433fb018feefa616171f
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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