Triethylamine → HCID 59153166, Verbindung

HRID 2355295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2355295
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][CH:37]=1.C(N(CC)CC)C>C(#N)C>[OH:43][CH2:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:7]([C:5]2[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=2)=[O:9])=[CH:37][CH:38]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 46738133[4-(Aminomethyl)phenyl]methanol--hydrogen chloride (1/1)

Produkt 1

HCID 59153166HCID 59153166, VerbindungAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Stir a mixture of 1-methyl-1H-imidazole-4-carboxylic acid (4.0 g, 31.67 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.6 g, 34.5 mmol) and 1-hydroxybenzotriazole hydrate (5.29 g, 34.5 mmoles) in anhydrous acetonitrile (150 mL) at room temperature for 1 hr. Add to the reaction mixture (4-aminomethyl-phenyl)-methanol hydrochloride (5.0 g, 28.8 mmol) and triethylamine (8.4 mL, 60.5 mmol). Stir the reaction mixture at room temperature overnight. Quench the reaction mixture with water and extract with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the title compound (4.6 g, 18.8 mmol). MS (m/z): 246 (M+1).

Aufarbeitung

  1. stirringStir the reaction mixture at room temperature overnight
  2. customQuench the reaction mixture with water
  3. extractionextract with ethyl acetate (3×)
  4. washCombine the organic layers, wash with brine
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-55368f18428e40f697f4493b7f12df8b
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754742B2

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