Dichloromethane → Carbonic acid di-2-pyridyl ester

HRID 864472Notes

Reaction equation

HRID 864472 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl[C:9](Cl)([O:11][C:12](=[O:18])[O:13]C(Cl)(Cl)Cl)Cl.O[C:21]1[CH:26]=[CH:25][CH:24]=C[N:22]=1.[CH2:27](Cl)Cl>>[N:22]1[CH:21]=[CH:26][CH:25]=[CH:24][C:9]=1[O:11][C:12](=[O:18])[O:13][C:6]1[CH:7]=[CH:27][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 94429TriphosgeneHCID 178516071HCID 178516071, compound

Product 1

HCID 2757370Carbonic acid di-2-pyridyl esterYield 57%

Procedure

Triethylamine (10.5 ml, 75 mmol) was added slowly to a solution of triphosgene (3.0 g, 10 mmol) and 2-hydroxypyridine (5.7 g, 60 mmol) in dry DCM (500 ml) at 0° C. under argon. The mixture was allowed to warm to room temperature and was stirred overnight. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate (500 ml), washed with saturated aqueous sodium hydrogen carbonate (2×150 ml) and brine (200 ml), dried over anhydrous sodium sulphate filtered and concentrated to give an orange oil. Crystallisation from ethyl acetate/hexane gave dipyrid-2-ylcarbonate as an off-white crystalline solid (3.70 g, 57%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with saturated aqueous sodium hydrogen carbonate (2×150 ml) and brine (200 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange oil
  7. customCrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-93d0ae53adf741138c110ade0964f905
Source dataset
uspto-grants-1996_10
Patent number
US05563151

Reaction notes

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