Benzoyl isocyanate → N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide

HRID 471634

Reaction equation

HRID 471634 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:11]([N:19]=[C:20]=[O:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCOCC1>[C:7]([C:6]1[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=1[NH:1][C:20]([NH:19][C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:21])#[N:8]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Product 1

HCID 57456902N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamideYield 84.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (1680 g, 11.04 mol) in 1,4-dioxane (42 L) was added benzoylisocyanate (1624 g, 11.04 mol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The resulting precipitate was collected by filtration, washed with 1,4-dioxane (3×1.7 l) and heptane (3×1.7 L), and dried under vacuum overnight to give N-(3-Cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide as a white solid (2800 g, 84.7% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.10 (s, 3H), 2.24 (s, 3H), 7.52-7.56 (m, 2H), 7.64-7.69 (m, 1H), 8.01-8.03 (m, 2H), 11.57 (brs, 1H), 12.05 (brs, 1H). MS 300 (MH+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with 1,4-dioxane (3×1.7 l) and heptane (3×1.7 L)
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-2a967f5d6e1a4e03a619985ce60fc982
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Linked notes

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