Ethyl isocyanate → HCID 21561590, compound

HRID 1581134Notes

Reaction equation

HRID 1581134 reaction equation
Cl.[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:11])[C:7]([CH3:10])=[N:8][CH:9]=1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>N1C=CC=CC=1>[CH2:12]([NH:14][C:15]([O:11][C:6]1[C:7]([CH3:10])=[N:8][CH:9]=[C:4]([CH2:3][O:2][C:15](=[O:16])[NH:14][CH2:12][CH3:13])[CH:5]=1)=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 1991873-Pyridinemethanol, 5-hydroxy-6-methyl-, hydrochloride

Product 1

HCID 21561590HCID 21561590, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.9 g. of 5-hydroxymethyl-2-methyl-3-pyridinol hydrochloride in 10 ml. of pyridine was added 0.8 g. of ethyl isocyanate and the mixture was stirred at 100°C for 2 hours. After cooling, the mixture was poured into ice water and extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off to give a crystalline product, which was recrystallized from ethyl acetate-n-hexane to give 0.95 g. of the desired product as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customto give a crystalline product, which
  7. customwas recrystallized from ethyl acetate-n-hexane
  8. customto give 0.95 g

Sources & evidence

ORD record
ord-9ec0ca0d77414835bde58d541545de13
Source dataset
uspto-grants-1976_01
Patent number
US03935311

Reaction notes

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