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

HRID 27381

Reaction equation

HRID 27381 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-cb5192f8f86244b28cb277a0844b27e9
Source dataset
uspto-grants-1980_09
Patent number
US04221737

Linked notes

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