Thiophosgene → 2-chloro-5-isothiocyanatopyridine

HRID 1713069Notes

Reaction equation

HRID 1713069 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:9](Cl)(Cl)=[S:10]>C(Cl)Cl.O>[Cl:8][C:5]1[CH:4]=[CH:3][C:2]([N:1]=[C:9]=[S:10])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 793055-Amino-2-chloropyridine

Product 1

HCID 187705802-chloro-5-isothiocyanatopyridineYield 101.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-amino-2-chloropyridine (5.0 g, 38.11 mmol) and thiophosgene (3.6 ml, 45.73 mmol) in DCM (75 ml) and water (35 ml) was stirred at r.t. for 18 h. The organic phase was dried (Na2SO4) and evaporated in vacuo to give the title compound as an off-white solid (6.6 g, 95%). δH (CDCl3) 8.35 (1H, dd, J 0.5, 2.2 Hz), 7.54 (1H, dd, J 2.2, 8.5 Hz), 7.40 (1H, dd, J 0.5, 8.5 Hz). LCMS (ES+) RT 3.61 minutes, 171 (M+H)+.

Workup

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-6efb041943684934887d18cc406c796b
Source dataset
uspto-grants-2010_09
Patent number
US07795256B2

Reaction notes

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