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

HRID 1641898Notes

Reaction equation

HRID 1641898 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>ClCCl>[C:21]1([O:20][C:18](=[O:19])[NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 15891Phenyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino pyridine (500 mg, 5.3 mmol) and N,N-diisopropylethylamine (685 mg, 5.3 mmol) are dissolved in dichloromethane (5 ml). Phenyl chloroformate (830 mg, 5.3 mmol) is added to the reaction mixture. The reaction mixture is stirred at room temperature for 72 hours. The reaction mixture is partitioned between dichloromethane and saturated NaHCO3 (aq). The aqueous is washed with dichloromethane (×2). The organics are combined, dried (MgSO4), filtered and reduced in vacuo to give the title compound.

Workup

  1. customThe reaction mixture is partitioned between dichloromethane and saturated NaHCO3 (aq)
  2. washThe aqueous is washed with dichloromethane (×2)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f1478a972fac4b6e8495e864bf2e4684
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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