But-2-yn-1-amine → HCID 178449099, compound

HRID 2050354Notes

Reaction equation

HRID 2050354 reaction equation
[N+:1]([CH:4]=[C:5](SC)[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[CH3:16])([O-:3])=[O:2].[CH2:19]([NH2:23])[C:20]#[C:21][CH3:22]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:23][CH2:19][C:20]#[C:21][CH3:22])[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[CH3:16])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 12599998But-2-yn-1-amineHCID 178503826HCID 178503826, compound

Product 1

HCID 178449099HCID 178449099, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-nitro-2-methylthio-2-{2-[(4-methyl-1H-imidazol-5-yl)methylthio]ethylamino}ethylene (2.25 g, 7.8 mmole) and 2-butyn-1-amine (2.16 g, 31.2 mmole) in acetonitrile (35 ml) was stirred under a positive pressure of nitrogen at reflux temperature for 7 hours and at room temperature for 15 hours. The solvent was removed by evaporation under reduced pressure, and the residue placed on silica gel and chromatographed by gradient elution using methylene chloride-methanol. The appropriate fractions yielded 1.93 g (80%) of the title product from acetonitrile. Recrystallization from isopropyl alcohol gave the product with mp 147.5°-151°.

Workup

  1. temperatureat reflux temperature for 7 hours
  2. customThe solvent was removed by evaporation under reduced pressure
  3. customchromatographed by gradient elution

Sources & evidence

ORD record
ord-7061474c2641419e8d05494a9c4f66df
Source dataset
uspto-grants-1980_04
Patent number
US04200760

Reaction notes

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