Benzyl Alcohol → Benzyl (5-n-butyl-2-pyridyl)carbamate

HRID 1112517Notes

Reaction equation

HRID 1112517 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([C:22]1[CH:23]=[CH:24][C:25](C(O)=O)=[N:26][CH:27]=1)[CH2:19][CH2:20][CH3:21].C([N:33]([CH2:36]C)CC)C.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCOCC1>[CH2:18]([C:22]1[CH:23]=[CH:24][C:25]([NH:33][C:36](=[O:8])[O:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:26][CH:27]=1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 3442Fusaric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 53891397Benzyl (5-n-butyl-2-pyridyl)carbamateYield 57.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diphenylphosphoryl azide (1.5 g., 5.58 mmoles) was added to a solution of 5-n-butylpyridine-2-carboxylic acid (1.0 g., 5.58 mmoles), triethylamine (0.565 g., 5.58 mmoles), and benzyl alcohol (0.663 g., 6.12 mmoles) in 1,4-dioxane (9.0 ml.) at 25°. The stirred solution was heated until an exothermic reaction began. When the exothermic reaction had subsided, the solution was heated under reflux for 1.5 hours. The reaction mixture was concentrated and the residue dissolved in toluene. This solution was washed successively with water, 10% aqueous sodium bicarbonate, and brine, and then dried over sodium sulfate. The solution was concentrated and the residue recrystallized from 2-propanol to give the title compound (0.91 g., 57%), m.p. 142°-143°.

Workup

  1. temperatureThe stirred solution was heated until an exothermic reaction
  2. customWhen the exothermic reaction
  3. temperaturethe solution was heated
  4. temperatureunder reflux for 1.5 hours
  5. concentrationThe reaction mixture was concentrated
  6. dissolutionthe residue dissolved in toluene
  7. washThis solution was washed successively with water, 10% aqueous sodium bicarbonate, and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationThe solution was concentrated
  10. customthe residue recrystallized from 2-propanol

Sources & evidence

ORD record
ord-710ab0fe32a641c592b5acd455011d48
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

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