Propargylamine → HCID 178457409, compound

HRID 27380

Reaction equation

HRID 27380 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]([NH2:22])[C:20]#[CH:21]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:22][CH2:19][C:20]#[CH:21])[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 239041PropargylamineHCID 178503826HCID 178503826, compound

Product 1

HCID 178457409HCID 178457409, compoundYield 87%

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 prepared according to Belgian Pat. No. 814,941 (4.0 g, 0.014 mole) and distilled propargylamine (7.74 g, 0.14 mole) in acetonitrile (60 ml) was stirred at reflux temperature under a positive pressure of nitrogen for 18 hours. The reaction mixture was cooled, evaporated to dryness and then triturated under 20 ml of isopropyl alcohol to give the title compound (3.58 g, 87%). Column chromatography on silica gel by gradient elution using methylene chloride-methanol gave a pure sample; mp 159°-160° dec.

Workup

  1. customprepared
  2. temperatureat reflux temperature under a positive pressure of nitrogen for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. customevaporated to dryness
  5. customtriturated under 20 ml of isopropyl alcohol

Sources & evidence

ORD record
ord-988f2b78e6134f9c8ad9f36d5d102635
Source dataset
uspto-grants-1980_09
Patent number
US04221737

Linked notes

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