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

HRID 2076999Notes

Reaction equation

HRID 2076999 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-3148c9b4e0bc4b1596d2bc81ab892bb7
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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