Phenyl Isothiocyanate → HCID 20313835, compound

HRID 2419126Notes

Reaction equation

HRID 2419126 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11]N=N[C:8]=2[CH:12]=1)([O-:3])=[O:2].[C:13]1([N:19]=[C:20]=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:20](=[N:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:21][C:8]=2[CH:12]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 124949965-Nitro-1,2,3-benzothiadiazole

Product 1

HCID 20313835HCID 20313835, compound

Procedure

A solution of 5-nitro-1,2,3-benzothiadiazole (4.6 g) in 50 ml of phenylisothiocyanate is heated at 220° C under an inert atmosphere until the evolution of nitrogen ceases (approximately 3 hours). The excess phenylisothiocyanate is removed in vacuo and the resultant residue chromatographed on 1000 ml of silica gel eluting with methylene chloride/pentane (1:4). The fractions containing the desired product are combined and concentrated in vacuo. The resultant solid is recrystallized from cyclohexane to yield 2.1 g of the title compound, melting point 136°-138° C.

Workup

  1. customThe excess phenylisothiocyanate is removed in vacuo
  2. customthe resultant residue chromatographed on 1000 ml of silica gel eluting with methylene chloride/pentane (1:4)
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated in vacuo
  5. customThe resultant solid is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-c19704cde94b404e89daf7a2114a0667
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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