Dimethylcarbamoyl Chloride → 3-Pyridyl diethylcarbamate

HRID 617299Notes

Reaction equation

HRID 617299 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.[CH2:8]([N:10]([CH2:13][CH3:14])[CH2:11]C)[CH3:9].CN(C)C(Cl)=[O:18]>C1C=CC=CC=1>[CH2:8]([N:10]([CH2:13][CH3:14])[C:11](=[O:18])[O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 79713-HydroxypyridineHCID 8471Triethylamine

Product 1

HCID 15126623-Pyridyl diethylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a refluxing solution of 3-pyridinol (9.7 g, 0.10 mol) and triethylamine (17.0 mL, 0.12 mol) in anhydrous benzene (300 mL) was slowly added a solution of N,N-dimethylcarbamyl chloride (14.4 mL, 0.11 mol) in anhydrous benzene (50 mL). After heating at reflux for 12 hours, the resultant mixture was filtered, and the salt was washed with benzene (3×10 mL). The filtrate was concentrated and distilled under reduced pressure to provide 18.4 g (95% yield) of the title compound as a light yellow oil (lit.: bp 91-93° C./3.5 mmHg, Millner, O. E, Jr.; Stanley, J. W; Purcell, W. P. J. Med. Chem. 1974, 17, 13). TLC Rf 0.57 (10:1 CHCl3 /MeOH). MS (DCI/NH3) m/e 212 (M+NH4)+, 195 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.44 (d, J=0.9 Hz, 1H, ArH), 8.43 (dd, J=4.8, 1.8 Hz, 1H, ArH), 7.53 (ddd, J=7.5, 1.8, 0.9 Hz, 1H, ArH), 7.30 (dd, J=7.5, 4.8 Hz, 1H, ArH), 3.43 (q, J=7.2 Hz, 2H, NCH2), 3.40 (q, J=7.2 Hz, 2H, NCH2), 1.27 (t, J=7.2 Hz, 3H, CH3), 1.21 (t, J=7.2 Hz, 3H, CH3).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 12 hours
  3. filtrationthe resultant mixture was filtered
  4. washthe salt was washed with benzene (3×10 mL)
  5. concentrationThe filtrate was concentrated
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-6f07d8bf0db94e1facc9d3ae0e775aa3
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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