Thiophosgene → 5-isothiocyanato-N,N,6-trimethylpyridin-2-amine

HRID 1398862Notes

Reaction equation

HRID 1398862 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH3:5][N:6]([CH3:15])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[N:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:10]1[CH:11]=[CH:12][C:7]([N:6]([CH3:5])[CH3:15])=[N:8][C:9]=1[CH3:14])=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 20748032N2,N2,6-trimethylpyridine-2,5-diamine

Product 1

HCID 866328865-isothiocyanato-N,N,6-trimethylpyridin-2-amineYield 43.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
0 °C

Procedure

Thiophosgene (1.3 mL, 16.7 mmol) was added dropwise to a stirred mixture of N2,N2,6-trimethylpyridine-2,5-diamine (2.30 g, 15.2 mmol) in tetrahydrofuran (20 mL) and saturated aqueous sodium hydrogen carbonate (20 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 diisopropyl ether to give the title compound as a pale yellow powder (1.27 g, 6.57 mmol, 43%).

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 diisopropyl ether

Sources & evidence

ORD record
ord-9602f15169cd42d3837b3b23852d8217
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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