Triethylamine → 2-Hydrazino-5-(methanesulfonyl)-pyridine

HRID 479867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479867
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][N:3]=1.C(N(CC)CC)C.O.[NH2:20][NH2:21]>O>[NH:20]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][N:3]=1)[NH2:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 98994832-Bromo-5-(methylsulfonyl)pyridine

Produkt 1

HCID 99642932-Hydrazino-5-(methanesulfonyl)-pyridineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A suspension of 2-bromo-5-(methanesulfonyl)-pyridine (7.3 g, 116 mmol), triethylamine (14.7 g, 145 mmol), and hydrazine hydrate (7.26 g, 145 mmol) in water (205 mL) was heated to 70° C. The reaction mixture became homogenous before the product started to precipitate out of this mixture (after 90 minutes). The reaction mixture was stirred at 70° C. for total of 5 hours and then was allowed to cool to room temperature and stirred for 18 hours. The precipitated product was collected by filtration, dried and recrystallized from hot ethanol to afford 2-hydrazinyl-5-(methanesulfonyl)-pyridine in 86% yield. Analytical data: 1H NMR (300 MHz, CDCl3) δ 3.12 (s, 3H), 4.44 (br s, 2H), 6.80 (br d, J=8.7 Hz, 1H), 7.81 (dd, J1=9.0 Hz, J2=2.4 Hz, 1H), 8.38 (d, 2.3 Hz, 1H), 8.57 (br s, 1H).

Aufarbeitung

  1. customto precipitate out of this mixture (after 90 minutes)
  2. temperatureto cool to room temperature
  3. stirringstirred for 18 hours
  4. filtrationThe precipitated product was collected by filtration
  5. customdried
  6. customrecrystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-25d4d701cebb455ea0abb22f87a47658
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06646128B2

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