Phenyl Isothiocyanate → HCID 20313842, compound

HRID 2419124Notes

Reaction equation

HRID 2419124 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10]N=N[C:7]=2[CH:11]=1.[C:12]1([N:18]=[C:19]=[S:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:19](=[N:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:20][C:7]=2[CH:11]=1

Participants

3

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 124949975-Methoxy-1,2,3-benzothiadiazole

Product 1

HCID 20313842HCID 20313842, compound

Procedure

A solution of 5-methoxy-1,2,3-benzothiadiazole (5 g) in 50 ml of phenyl isothiocyanate is heated at 220° C under an inert atmosphere until the evolution of nitrogen ceases (about two hours). The excess phenyl isothiocyanate is removed in vacuo. The resultant residue is chromatographed on silica gel (500 ml) eluting with pentane/dichloromethane (4:1). Fractions containing the desired product (Rf =0.2, silica gel, benzene) are combined and concentrated in vacuo. The resultant solid is recrystallized from pentane to yield 2.8 g of the title compound, melting point 58°-60° C.

Workup

  1. customThe excess phenyl isothiocyanate is removed in vacuo
  2. customThe resultant residue is chromatographed on silica gel (500 ml)
  3. washeluting with pentane/dichloromethane (4:1)
  4. additionFractions containing the desired product (Rf =0.2, silica gel, benzene)
  5. concentrationconcentrated in vacuo
  6. customThe resultant solid is recrystallized from pentane

Sources & evidence

ORD record
ord-ad62bddbb94e4999ad2b9ee154c5a48d
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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