Benzyl Isothiocyanate → 1,4-Di(benzylthiocarbamoylamino)benzene

HRID 756

Reaction equation

HRID 756 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.[CH2:9]([N:16]=[C:17]=[S:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C>[CH2:9]([NH:16][C:17]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([NH:8][C:17](=[S:18])[NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:2][CH:1]=1)=[S:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 7814P-Phenylenediamine

Product 1

HCID 196933051,4-Di(benzylthiocarbamoylamino)benzeneYield 61.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

p-Phenylenediamine (2.707 g, 25 mM) was dissolved in 20 ml of ethyl acetate, and 2 equivalents of benzylisothiocyanate (7.461 g, 50 mM) were added. The mixture was stirred at 80° C. for 30 minutes. After cooling, the reaction mixture was filtered, and washed with ethylacetate/n-hexane to obtain 6.26 g (61.6% yield) of a colorless crystal of compound A-25.

Workup

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

Sources & evidence

ORD record
ord-96af32b871984951b1483d8522037b06
Source dataset
uspto-grants-1998_03
Patent number
US05723075

Linked notes

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