Thiophosgene → 2,6-Dichloro-3-isothiocyanatopyridine

HRID 1177389Notes

Reaction equation

HRID 1177389 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([Cl:15])[N:9]=1.[C:16](Cl)(Cl)=[S:17]>C(Cl)Cl>[Cl:7][C:8]1[C:13]([N:14]=[C:16]=[S:17])=[CH:12][CH:11]=[C:10]([Cl:15])[N:9]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 1128462,6-Dichloro-3-pyridylamine

Product 1

HCID 715192602,6-Dichloro-3-isothiocyanatopyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of sodium carbonate (15.2 g, 144 mmol), 2,6-dichloropyridin-3-amine (9.00 g, 55.2 mmol), and thiophosgene (5.50 mL, 71.8 mmol) in 100 mL anhydrous DCM was allowed to stir in a sealed vessel for 2 days. The reaction mixture was filtered through a glass frit, rinsing with DCM. The filtrate was concentrated in vacuo to give 2,6-dichloro-3-isothiocyanatopyridine as a peach-colored solid.

Workup

  1. filtrationThe reaction mixture was filtered through a glass frit
  2. washrinsing with DCM
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d88cd8ee7a4e4e9e8f167200188416fb
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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