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

HRID 471540Notes

Reaction equation

HRID 471540 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) δ 11.33 (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-69bf55b654984461849dc3a4837a9bb1
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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