Diethyl Ether → 5-Chloro-2-isothiocyanatopyridine

HRID 1287480Notes

Reaction equation

HRID 1287480 reaction equation
[C:1](Cl)(Cl)=[S:2].CCOCC.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=1.C(=O)([O-])[O-].[Ca+2]>O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]=[C:1]=[S:2])=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 661742-Amino-5-chloropyridine

Product 1

HCID 123832235-Chloro-2-isothiocyanatopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 16.3 ml. of thiophosgene in 600 ml. of ether is added with rapid stirring to a suspension of 25.6 g. of 5-chloro-2-aminopyridine and 42 g. of calcium carbonate in 600 ml. of water. The reaction mixture is stirred for 11/2 hours and the ether layer separated and the water layer extracted with a 400 ml. portion of ether. The combined ether extracts are washed with water, dried over magnesium sulfate and evaporated to dryness in vacuo affording 29.9 g. of a dark red oil. The oil is distilled at 0.75 mm. of Hg. at a temperature 96° C. affording 5-chloro-2-pyridylisothiocyanate.

Workup

  1. stirringThe reaction mixture is stirred for 11/2 hours
  2. customthe ether layer separated
  3. extractionthe water layer extracted with a 400 ml
  4. washThe combined ether extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customaffording 29.9 g
  8. distillationThe oil is distilled at 0.75 mm. of Hg

Sources & evidence

ORD record
ord-cdc48d8599524745986046a5880acaa8
Source dataset
uspto-grants-1976_10
Patent number
US03984549

Reaction notes

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