Thiophosgene → 2-chloro-5-isothiocyanatopyridine

HRID 479505Notes

Reaction equation

HRID 479505 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[N:10][CH:11]=1>C(Cl)(Cl)Cl>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]([N:5]=[C:1]=[S:2])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 793055-Amino-2-chloropyridine

Product 1

HCID 187705802-chloro-5-isothiocyanatopyridineYield 56.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of thiophosgene (3.21 mL, 42.1 mmol) in chloroform (10 mL) was heated at reflux and treated with a solution of 5amino-2-chloropyridine (3.61 g, 28.1 mmol) in chloroform (25 mL) for 40 minutes. The solution was heated an additional 2 hours, the reaction mixture was cooled, and the solids formed were removed by filtration. Concentration of the filtrate provided 2.73 g of the desired product as a white solid.

Workup

  1. temperatureat reflux
  2. temperatureThe solution was heated an additional 2 hours
  3. temperaturethe reaction mixture was cooled
  4. customthe solids formed
  5. customwere removed by filtration

Sources & evidence

ORD record
ord-76ceb25cf7374bbe9df1b49db161f721
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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