Benzyl Alcohol → Benzyl (5-ethyl-2-pyridyl)carbamate

HRID 1701395Notes

Reaction equation

HRID 1701395 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([C:20]1[CH:21]=[CH:22][C:23](C(O)=O)=[N:24][CH:25]=1)[CH3:19].C([N:31]([CH2:34]C)CC)C.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1>[CH2:18]([C:20]1[CH:21]=[CH:22][C:23]([NH:31][C:34](=[O:8])[O:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:24][CH:25]=1)[CH3:19]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 1203755-Ethylpicolinic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 54145659Benzyl (5-ethyl-2-pyridyl)carbamateYield 50.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diphenylphosphoryl azide (4.04 g., 14.7 mmoles) was added to a solution of 5-ethylpyridine-2-carboxylic acid (2.22 g., 14.7 mmoles), triethylamine (1.485 g., 14.7 mmoles), and benzyl alcohol (1.75 g., 16.17 mmoles) in 1,4-dioxane (23.5 ml.), and the mixture heated under reflux for one hour. The 1,4-dioxane was removed under reduced pressure. A solution of the residue in toluene was washed successively with water, aqueous sodium bicarbonate, and brine, and was then dried over sodium sulfate. The toluene was removed and the residue recrystallized from 2-propanol to give benzyl (5-ethyl-2-pyridyl)carbamate (1.9 g., 50.5%), m.p. 125°-127°. An analytical sample had m.p. 127°-130°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for one hour
  3. customThe 1,4-dioxane was removed under reduced pressure
  4. washA solution of the residue in toluene was washed successively with water, aqueous sodium bicarbonate, and brine
  5. dry with materialwas then dried over sodium sulfate
  6. customThe toluene was removed
  7. customthe residue recrystallized from 2-propanol

Sources & evidence

ORD record
ord-584c724415a844308b013d3bae654d9a
Source dataset
uspto-grants-1980_03
Patent number
US04192944

Reaction notes

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