Phenyl Isothiocyanate → HCID 14171368, compound

HRID 1611739Notes

Reaction equation

HRID 1611739 reaction equation
[O-]CC.[Na+].[C:5](#[N:9])[CH2:6][C:7]#[N:8].[C:10]1([N:16]=[C:17]=[S:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH2:19]Cl>C(O)C>[NH2:8][C:7]1[C:6]([C:5]#[N:9])=[C:17]([NH:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:18][N:19]=1

Participants

6

Reactant 4

HCID 7673Phenyl IsothiocyanateHCID 8010MalononitrileHCID 25423MonochloramineHCID 2723922Sodium ethoxide

Product 1

HCID 14171368HCID 14171368, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cold solution of sodium ethoxide (1.7 g, 25 mmol) in absolute ethanol (25 ml) was added malononitrile (1.65 g, 25 mmol), followed by addition of phenyl isothiocyanate (5.43 g, 25 mmol). The mixture was stirred at ambient temperature for 12 hours, cooled and then treated with freshly prepared aqueous chloramine solution (125 ml). After being stirred for 24 hours at ambient temperature, the mixture was filtered and the solid was dried in air. Crystallization from DMF-EtOH afforded colorless crystals (2.5 g, 65%).

Workup

  1. temperaturecooled
  2. stirringAfter being stirred for 24 hours at ambient temperature
  3. filtrationthe mixture was filtered
  4. customthe solid was dried in air
  5. customCrystallization from DMF-EtOH afforded colorless crystals (2.5 g, 65%)

Sources & evidence

ORD record
ord-e6d189fad7124688a546737a036a7c64
Source dataset
uspto-grants-2006_01
Patent number
US06989451B2

Reaction notes

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