Triethylamine → 3-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

HRID 1849021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1849021
C([O:3][C:4](=O)/[N:5]=[C:6](\OCC)/[CH3:7])C.Cl.[CH:13]([NH:16][NH2:17])([CH3:15])[CH3:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:13]([N:16]1[C:4](=[O:3])[NH:5][C:6]([CH3:7])=[N:17]1)([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 855731-Isopropylhydrazine hydrochlorideHCID 13488724ethyl (1Z)-N-ethoxycarbonylethanimidate

Produkt 1

HCID 1363405273-methyl-1-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of [1-ethoxy-eth-(Z)-ylidene]-carbamic acid ethyl ester (834 mg, 5.24 mmol) in toluene (15 mL) was added isopropyl hydrazine hydrochloride (637 mg, 5.76 mmol) follwed by triethylamine (803 μL, 5.76 mmol). The reaction vessel was sealed and stirred at 45° C. for 45 minutes before the addition of triethylamine (803 μL, 5.76 mmol). The resultant mixture was heated to 90° C. and stirred for 17 hours, then cooled and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, gradient 0% to 8% 2M NH3/MeOH in DCM) to give 2-Isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one as an off white solid (329 mg, 44%). LCMS: RT=2.16 min, [M+Na]+=164

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by flash chromatography (SiO2, gradient 0% to 8% 2M NH3/MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-ee721cbe99f44e76b51a40df006c6af3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952043B2

Notizen zur Reaktion

Wird geladen…