Phenyl Isothiocyanate → 4,4'-Di(phenylthiocarbamoylamino)benzanilide

HRID 754

Reaction equation

HRID 754 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.[C:18]1([N:24]=[C:25]=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:18]1([NH:24][C:25]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:25](=[S:26])[NH:24][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:11][CH:10]=3)=[O:7])=[CH:4][CH:3]=2)=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 699174,4'-Diaminobenzanilide

Product 1

HCID 196932814,4'-Di(phenylthiocarbamoylamino)benzanilideYield 72.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

4,4'-Diaminobenzanilide (0.658 g, 2.5 mM) was dissolved in 20 ml of acetone, and 2 equivalents of phenylisothiocyanate (0.676 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 0.90 g (72.3% yield) of a colorless crystal of compound A-15.

Workup

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

Sources & evidence

ORD record
ord-e8642ae0ecb248809067cd131fde0eed
Source dataset
uspto-grants-1998_03
Patent number
US05723075

Linked notes

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