Propargylamine → N-[1-(Methylsulfanyl)-2-nitroethenyl]prop-2-yn-1-amine

HRID 894126Notes

Reaction equation

HRID 894126 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[CH3:5][S:6]([C:8](SC)=[CH:9][N+:10]([O-:12])=[O:11])=O>CO>[CH3:5][S:6][C:8]([NH:4][CH2:1][C:2]#[CH:3])=[CH:9][N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 71401969N-[1-(Methylsulfanyl)-2-nitroethenyl]prop-2-yn-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of propargylamine (1.10 g, 0.02 mole) in 22 ml of methanol was added dropwise to a stirred suspension of 1-methylsulfinyl-1-methylthio-2-nitroethylene [prepared according to the procedure described in Belgian Pat. No. 841,526] at 25°. After 1 hour at ambient temperature, the solution was evaporated under reduced pressure, triturated under 20 ml of cold isopropyl alcohol and filtered to give product. Recrystallization from isopropyl alcohol gave 1-methylthio-1-(2-propynylamino)-2-nitroethylene; mp 131°-132°.

Workup

  1. customprepared
  2. customat 25°
  3. customthe solution was evaporated under reduced pressure
  4. customtriturated under 20 ml of cold isopropyl alcohol
  5. filtrationfiltered
  6. customto give product
  7. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-053f7501bbcf43b784c4b3e26c9bbcce
Source dataset
uspto-grants-1981_08
Patent number
US04282363

Reaction notes

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