Dichloromethane → Carbonic acid di-2-pyridyl ester

HRID 439829Notes

Reaction equation

HRID 439829 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, 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. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange oil
  7. customCrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a693da3b50fa440db45cdf32a5ee4574
Source dataset
uspto-grants-1996_05
Patent number
US05516783

Reaction notes

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