Benzoyl isothiocyanate → N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

HRID 44334

Reaction equation

HRID 44334 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]=[S: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)=[S:21])#[N:8]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Product 1

HCID 899430N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (1.52 g, 10.0 mmol) in 1.4-dioxane (20 mL) was added benzoylisothiocyanate (1.63 g, 10.0 mmol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The precipitation was collected by filtration, washed with EtOAc/Hexanes (1:4), and dried under vacuum overnight to give N-(3-Cyano-4,5-dimethylthiophen-2-ylcarbamothioyl)benzamide as a white solid. 1H NMR (400 MHz, CDCl3) δ2.23 (s, 3H), 2.31 (s, 3H), 7.58-7.54 (m, 2H), 7.68-7.66 (m, 1H), 7.94 (d, J=7.2 Hz, 2H), 9.13 (bs, 1H). MS 316 (MH+).

Workup

  1. customThe precipitation
  2. filtrationwas collected by filtration
  3. washwashed with EtOAc/Hexanes (1:4)
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-9f8d0ac715214716a431791d8beae02d
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Linked notes

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