4-Aminopyridine → Carbamic acid, 4-pyridinyl-, phenyl ester

HRID 49771

Reaction equation

HRID 49771 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[N:15]1[CH:16]=[CH:17][C:12]([NH:11][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 15891Phenyl chloroformate

Product 1

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenyl chloroformate (5.64 g) in dichloromethane (70 ml) was added a solution of 4-aminopyridine (2.84 g) and triethylamine (5.02 ml) in dichloromethane (100 ml) dropwise under cooling on an ice-water bath. After stirring for 1 hour, the solvents were removed under reduced pressure. A residue was diluted with dichloromethane (200 ml) and water (200 ml). An organic phase was separated and washed with water and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. The reaction mixture was diluted with diisopropyl ether and the precipitates were filtered. After rinse with diethyl ether, O-phenyl N-(4-pyridyl)carbamate (5.07 g) was obtained.

Workup

  1. temperatureunder cooling on an ice-water bath
  2. customthe solvents were removed under reduced pressure
  3. additionA residue was diluted with dichloromethane (200 ml) and water (200 ml)
  4. customAn organic phase was separated
  5. washwashed with water and brine
  6. dry with materialAfter drying with magnesium sulfate
  7. customthe solvents were removed under reduced pressure
  8. additionThe reaction mixture was diluted with diisopropyl ether
  9. filtrationthe precipitates were filtered
  10. washAfter rinse with diethyl ether

Sources & evidence

ORD record
ord-9dacb9240a3644f7b68c0ff696ee87d3
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

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