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

HRID 2077025Notes

Reaction equation

HRID 2077025 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-56891b8d43d6484b8dec9f3f9d568a87
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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