Thiophosgene → 5-isothiocyanato-N,N,4-trimethylpyridin-2-amine

HRID 1398860Notes

Reaction equation

HRID 1398860 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][N:6]([CH3:15])[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([NH2:14])=[CH:9][N:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:14]([C:10]1[C:11]([CH3:13])=[CH:12][C:7]([N:6]([CH3:15])[CH3:5])=[N:8][CH:9]=1)=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 22136281N2,N2,4-trimethylpyridine-2,5-diamine

Product 1

HCID 866328825-isothiocyanato-N,N,4-trimethylpyridin-2-amineYield 70.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
0 °C

Procedure

Thiophosgene (9.3 mL, 125 mmol) was added dropwise to a stirred mixture of N2,N2,4-trimethylpyridine-2,5-diamine (15.7 g) 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 (14.1 g, 73.0 mmol, 70% in 2 steps).

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-0a47aaf55c734cb9be8c7df4772da2ae
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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