But-3-yn-2-amine → HCID 178449098, compound

HRID 2050355

Reaction equation

HRID 2050355 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].[NH2:19][CH:20]([CH3:23])[C:21]#[CH:22]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:19][CH:20]([C:21]#[CH:22])[CH3:23])[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 10290734But-3-yn-2-amineHCID 178503826HCID 178503826, compound

Product 1

HCID 178449098HCID 178449098, compound

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 (3.13 g, 10.9 mmole) and 3-amino-1-butyne (4.5 g, 65.1 mmole) in acetonitrile (45 ml) was stirred at reflux temperature under a positive pressure of nitrogen for 17 hours. The reaction mixture was evaporated under reduced pressure then the residue placed on silica gel and chromatographed by gradient elution using methylene chloride-methanol. Recrystallization yielded the title compound.

Workup

  1. temperatureat reflux temperature under a positive pressure of nitrogen for 17 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customchromatographed by gradient elution
  4. customRecrystallization

Sources & evidence

ORD record
ord-5d16ed2a706741fb834ea9448094c043
Source dataset
uspto-grants-1980_04
Patent number
US04200760

Linked notes

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