Thiophosgene → 5-Isothiocyanato-2-methoxy-4-methylpyridine

HRID 1628504Notes

Reaction equation

HRID 1628504 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[CH:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:10]1[C:9]([CH3:14])=[CH:8][C:7]([O:6][CH3:5])=[N:12][CH:11]=1)=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 2431706-Methoxy-4-methylpyridin-3-amine

Product 1

HCID 866328845-Isothiocyanato-2-methoxy-4-methylpyridineYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
0 °C

Procedure

Thiophosgene (8.9 mL, 120 mmol) was added dropwise to a stirred mixture of 6-methoxy-4-methylpyridin-3-amine (13.8 g, 99.8 mmol) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at 0° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give the title compound as a colorless powder (10.6 g, 58.8 mmol, 59%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-d58f7c4ea590430d89cdd1f3eba84567
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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