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

HRID 711607Notes

Reaction equation

HRID 711607 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 90.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (example 4b) (25 g, 164.5 mmol) in 1,4-dioxane (600 mL) was added benzoyl isocyanate (24.2 g, 164.5 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitate was collected by filtration, washed with 1,4-dioxane (20 mL×3), and dried under vacuum at 40° C. for 3 hours to give N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide (44.35 g, 90%) as a white solid. 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 precipitate was collected by filtration
  2. washwashed with 1,4-dioxane (20 mL×3)
  3. customdried under vacuum at 40° C. for 3 hours

Sources & evidence

ORD record
ord-196f4e94aead487a93a220a5f4d07e20
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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