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

HRID 1357331Notes

Reaction equation

HRID 1357331 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 (27.5 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 triturated with hot ethanol to afford 2-hydrazino-5-(methanesulfonyl)-pyridine in 86% yield. 1H NMR (300 MHz, CDCI3) δ3.12 (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. customtriturated with hot ethanol

Sources & evidence

ORD record
ord-c8f8f1c43e524cbcbc622e65c5c1257c
Source dataset
uspto-grants-2003_07
Patent number
US06590103B2

Reaction notes

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