Thiophosgene → 3-Isothiocyanato-4-methoxypyridine

HRID 2403040Notes

Reaction equation

HRID 2403040 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([O-])(O)=O.[Na+].[C:15](Cl)(Cl)=[S:16]>C(Cl)(Cl)Cl.O>[N:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9])=[C:15]=[S:16]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 52003433-Amino-4-methoxypyridine

Product 1

HCID 866653953-Isothiocyanato-4-methoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 3-amino-4-methoxypyridine (2.01 g, 16.2 mmol) and NaHCO3 (4.08 g, 48.6 mmol) in CHCl3 and water (1:1, 50 mL) at 4° C. was added thiophosgene (1.5 mL, 19.6 mmol) dropwise. After completion of the addition, the ice bath was removed. The mixture was stirred for 4 hours, the organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phases were washed with water, dried over Na2SO4, filtered, and concentrated to give the title compound as brown solid.

Workup

  1. additionAfter completion of the addition
  2. customthe ice bath was removed
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-087e5bee018c44f992ec7fdb077cf58f
Source dataset
uspto-grants-2014_08
Patent number
US08798939B2

Reaction notes

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