Benzoyl isothiocyanate → 1,4-Di(benzoylthiocarbamoylamino)-2,5-dimethylbenzene

HRID 757

Reaction equation

HRID 757 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][C:3]=1[NH2:10].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)(=O)C>[C:11]([NH:19][C:20]([NH:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH:10][C:20](=[S:21])[NH:19][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:5]=1[CH3:9])=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 1608242,5-Dimethyl-p-phenylenediamine

Product 1

HCID 196932491,4-Di(benzoylthiocarbamoylamino)-2,5-dimethylbenzeneYield 98.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,5-Dimethyl-p-phenylenediamine (0.340 g, 2.5 mM) was dissolved in 30 ml of ethyl acetate, and 2 equivalents of benzoylisothiocyanate (0.816 g, 5 mM) were added. The mixture was stirred at room temperature for 10 minutes. After cooling, the reaction mixture was filtered, and washed with ethyl acetate/n-hexane to obtain 1.14 g (98.6% yield) of a colorless crystal of compound A-26.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washwashed with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-86468e176b4c448b95c93ea7f5a809d2
Source dataset
uspto-grants-1998_03
Patent number
US05723075

Linked notes

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