Phenyl Isothiocyanate → HCID 20313826, compound

HRID 2419127Notes

Reaction equation

HRID 2419127 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]2[S:10]N=N[C:7]=2[CH:11]=1.[C:14]1([N:20]=[C:21]=[S:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:21](=[N:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:22][C:7]=2[CH:11]=1

Participants

3

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 12494995HCID 12494995, compound

Product 1

HCID 20313826HCID 20313826, compound

Procedure

A solution of 5-(trifluoromethyl)-1,2,3-benzothiadiazole (5 g) in 50 ml of phenylisothiocyanate is heated at reflux under an inert atmosphere until the evolution of nitrogen ceases (approximately 3 hours). The excess phenyl isothiocyanate is removed by distillation. The residue is chromatographed on 1000 ml of silica gel eluting with pentane/dichloromethane (4:1). Fractions containing the desired product are combined and concentrated in vacuo. The resultant solid is recrystallized from hexane to yield 4 g of the title compound, melting point 122°-123° C.

Workup

  1. temperatureat reflux under an inert atmosphere until the evolution of nitrogen ceases (approximately 3 hours)
  2. customThe excess phenyl isothiocyanate is removed by distillation
  3. customThe residue is chromatographed on 1000 ml of silica gel eluting with pentane/dichloromethane (4:1)
  4. additionFractions containing the desired product
  5. concentrationconcentrated in vacuo
  6. customThe resultant solid is recrystallized from hexane

Sources & evidence

ORD record
ord-2fc60bbed43d4d6883bbf71ccc9c9f1f
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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