Benzoyl isocyanate → N-(2-cyanocyclopent-1-enylcarbamoyl)benzamide

HRID 44410Notes

Reaction equation

HRID 44410 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]#[N:8].[C:9]([N:17]=[C:18]=[O:19])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCOCC1>[C:7]([C:3]1[CH2:4][CH2:5][CH2:6][C:2]=1[NH:1][C:18]([NH:17][C:9](=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:19])#[N:8]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 2872752-Aminocyclopent-1-ene-1-carbonitrile

Product 1

HCID 57456937N-(2-cyanocyclopent-1-enylcarbamoyl)benzamideYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-aminocyclopent-1-enecarbonitrile (400 mg, 3.7 mmol) in 1.4-dioxane (20 mL) was added benzoyl isocyanate (545 g, 3.7 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitate was collected by filtration, washed with 1.4-dioxane, and dried to give N-(2-cyanocyclopent-1-enylcarbamoyl)benzamide (720 mg, 76%) as a white solid. 1H NMR (400 MHz, CDCl3) δ11.33 (s, 1H), 11.22 (brs, 1H), 7.99-7.97 (m, 2H), 7.67-7.63 (m, 1H), 7.54-7.51 (m, 2H), 3.04-3.0 (m, 2H), 2.51-2.47 (m, 2H) 1.95-1.90 (m, 2H). MS 256 (MH+).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 1.4-dioxane
  3. customdried

Sources & evidence

ORD record
ord-006eac9d25614c4c8ac3ea2cdb6cfe22
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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