Benzyl Isothiocyanate → 4,4'-Di(benzylthiocarbamoylamino)benzanilide

HRID 755

Reaction equation

HRID 755 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:18]([N:25]=[C:26]=[S:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([NH:25][C:26]([NH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:26](=[S:27])[NH:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1)=[S:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 699174,4'-Diaminobenzanilide

Product 1

HCID 196932974,4'-Di(benzylthiocarbamoylamino)benzanilideYield 43.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

4,4'-Diaminobenzanilide (0.568 g, 2.5 mM) was dissolved in 20 ml of acetone, and 2 equivalents of benzylisothiocyanate (0.746 g, 5 mM) was added. The mixture was stirred at 55° C. for 10 minutes. After cooling, the reaction mixture was filtered, and washed with acetone/n-hexane to obtain 0.57 g (43.4% yield) of a colorless crystal of compound A-16.

Workup

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

Sources & evidence

ORD record
ord-83e2d9b7b08846c09e3e4e23f2dc9784
Source dataset
uspto-grants-1998_03
Patent number
US05723075

Linked notes

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