Propargylamine → 1-Nitro-2-(propynylamino)-2-{2-[(2-pyridyl)methylthio]ethylamino)ethylene

HRID 1577909Notes

Reaction equation

HRID 1577909 reaction equation
[N+:1]([CH:4]=[C:5](SC)[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([O-:3])=[O:2].[CH2:19]([NH2:22])[C:20]#[CH:21]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:22][C:19]#[C:20][CH3:21])[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 705703291-Nitro-2-methylthio-2-[2-(2-pyridylmethylthio)ethylamino]ethylene

Product 1

HCID 705701261-Nitro-2-(propynylamino)-2-{2-[(2-pyridyl)methylthio]ethylamino)ethylene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product of Step A (2.0 g; 7.03 mmoles) and propargylamine (3.44 g; 62.5 mmoles) in acetonitrile (30 ml) was stirred and heated to reflux temperature under a positive pressure of nitrogen for 1.5 hours then stirred at ambient temperature for 42 hours. The reaction mixture was filtered and the product collected. Recrystallization from acetonitrile gave the title compound; mp 147°-148°.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature under a positive pressure of nitrogen for 1.5 hours
  3. stirringthen stirred at ambient temperature for 42 hours
  4. filtrationThe reaction mixture was filtered
  5. customthe product collected
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-7075421de02d49d89db4a5e11911db4b
Source dataset
uspto-grants-1981_09
Patent number
US04289876

Reaction notes

Loading…