Thiophosgene → 2-Chloro-5-isothiocyanatopyridine
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- dry with materialThe organic phase was dried (Na2SO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-6efb041943684934887d18cc406c796b
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795256B2
Reaction notes
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