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

HRID 1112515
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1112515
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 54145659Benzyl (5-ethyl-2-pyridyl)carbamateAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dca56abc36b64abea6f6f69d395ae3f9
Quelldatensatz
uspto-grants-1978_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04122274

Notizen zur Reaktion

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