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

HRID 471515Notes

Reaction equation

HRID 471515 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-95c151ed9ae64d8385c4b3b923d7a0f2
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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