Phenyl Isothiocyanate → 5-Chloro-N-phenyl-1,3-benzodithiol-2-imine

HRID 2419122Notes

Reaction equation

HRID 2419122 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[S:18]N=N[C:15]=2[CH:19]=1>>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[S:18][C:8](=[N:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[S:9][C:15]=2[CH:19]=1

Participants

3

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 124949945-Chlorobenzo[d][1,2,3]thiadiazole

Product 1

HCID 203138485-Chloro-N-phenyl-1,3-benzodithiol-2-imineYield 24.6%

Conditions

Temperature
220 °C

Procedure

Phenylisothiocyanate (8.8g) and 5-chloro-1,2,3-benzothiadiazole (3.75g) are combined under an inert atmosphere and heated at 220° C until nitrogen evolution ceases. Initial purification of the product is accomplished by dry column chromatography (600g alumina column, benzene solvent). The product is further purified with a methylene chloride wash and recrystallization (twice) from pentane to yield 1.5g of the title compound, melting point 71°-73° C.

Workup

  1. customInitial purification of the product
  2. dry with materialby dry column chromatography (600g alumina column, benzene solvent)
  3. customThe product is further purified with a methylene chloride
  4. washwash
  5. customrecrystallization (twice) from pentane

Sources & evidence

ORD record
ord-f202f30cfad24635a7747b126d4a240b
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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