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

HRID 1761257Notes

Reaction equation

HRID 1761257 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d09787e97bac450fa8fa0085699f75e8
Source dataset
uspto-grants-2005_01
Patent number
US06846930B2

Reaction notes

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