Hydrochloric Acid → 3,5-Dichloro-2-isothiocyanatopyridine

HRID 27901

Reaction equation

HRID 27901 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[N-]=[C:12]=[S:13]>>[Cl:1][C:2]1[C:3]([N:9]=[C:12]=[S:13])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 778863,5-Dichloro-3-pyridylamineHCID 178418790HCID 178418790, compound

Product 1

HCID 233404453,5-Dichloro-2-isothiocyanatopyridine

Procedure

3,5-Dichloro-2-amino pyridine (8.15, 0.05 mol) was treated with thiophosgenes (10% soln. in toluene, 55 ml). The mixture was refluxed until clear solution was obtained and no further hydrochloric acid gas was being evolved. The mixture was cooled, and the solid which crystallised was removed by filtration. The mother liquors, after evaporation and crystallisation of the residual oil, yielded 5.5 g. (55%) of the required isothiocyanate as pale yellow needles m. pt. 45°-6°.

Workup

  1. temperatureThe mixture was refluxed until clear solution
  2. customwas obtained
  3. temperatureThe mixture was cooled
  4. customthe solid which crystallised
  5. customwas removed by filtration
  6. customThe mother liquors, after evaporation and crystallisation of the residual oil
  7. customyielded 5.5 g

Sources & evidence

ORD record
ord-dffacfefda164193be659bca22101673
Source dataset
uspto-grants-1980_09
Patent number
US04224331

Linked notes

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