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Potassium Carbonate → [2-(4-Bromopyrazol-1-yl)ethyl]dimethylamine

HRID 64049
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64049
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Produkt 1

HCID 21859709[2-(4-Bromopyrazol-1-yl)ethyl]dimethylamineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-1H-pyrazole (5 g, 34 mmol) in DMF were added K2CO3 (11.75 g, 85.03 mmol, 2.5 eq.) and 2-chloro-N,N-dimethylethanamine HCl (7.35 g, 51 mmol, 1.5 eq) and the mixture was stirred at RT for 12 h. The mixture was quenched with water and extracted with DCM (3×150 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 1% methanol in DCM) to give the product in 86% yield (6.4 g). 1H NMR (300 MHz, DMSO-d6): δ 7.95 (s, 1H), 7.25 (s, 1H), 4.18 (t, 2H), 2.61 (t, 2H), 2.15 (s, 6H); LC-MS (ESI): Calculated mass: 218.09; Observed mass: 219.8[M+H]+ (RT: 0.439 min).

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with DCM (3×150 ml)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-1a0d515778a9411c8eef06070d89d8c2
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09447091B2

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