Benzoyl isocyanate → N-(3-cyanopyridin-2-ylcarbamoyl)benzamide

HRID 711653Notes

Reaction equation

HRID 711653 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]([N:18]=[C:19]=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCOCC1>[C:8]([C:7]1[C:2]([NH:1][C:19]([NH:18][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:20])=[N:3][CH:4]=[CH:5][CH:6]=1)#[N:9]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 8182592-Amino-3-cyanopyridine

Product 1

HCID 57456924N-(3-cyanopyridin-2-ylcarbamoyl)benzamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-3-cyanopyridine (300 mg, 2.5 mmol) in 1,4-dioxane (5 mL) was added benzoyl isocyanate (370 mg, 2.5 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitation was collected by filtration, washed with EtOAc/Hexanes (1:4), and dried under vacuum to give N-(3-cyanopyridin-2-ylcarbamoyl)benzamide as a white solid (360 mg, 54%). MS 266 (MH+).

Workup

  1. customThe precipitation
  2. filtrationwas collected by filtration
  3. washwashed with EtOAc/Hexanes (1:4)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c9bb0161a97f44b5a80e6aee66ff2a4d
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…