Thiophosgene → 2,4-Dichloro-5-isothiocyanatopyridine

HRID 1177513Notes

Reaction equation

HRID 1177513 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[NH2:9].C(=O)([O-])[O-].[Na+].[Na+].[C:16](Cl)(Cl)=[S:17]>C(Cl)Cl>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:9]=[C:16]=[S:17])=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 5957294,6-Dichloropyridin-3-amine

Product 1

HCID 866387192,4-Dichloro-5-isothiocyanatopyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring slurry of 4,6-dichloropyridin-3-amine (2.00 g, 12 mmol) and sodium carbonate (3.4 g, 32 mmol) in 10 mL DCM was added thiophosgene (1.2 mL, 16 mmol). The orange mixture was sealed and allowed to stir at ambient temperature overnight. The reaction mixture was filtered, rinsing with DCM, and the filtrate concentrated in vacuo to give 2,4-dichloro-5-isothiocyanatopyridine as an orange solid. MS (ESD m/z: calculated: 203.9; Observed: 204.9 (M++1).

Workup

  1. customThe orange mixture was sealed
  2. filtrationThe reaction mixture was filtered
  3. washrinsing with DCM
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-539069a83c114ca393b26939ec82fbf7
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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