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

HRID 27393Notes

Reaction equation

HRID 27393 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 Patent 841,353], at 25°. After 1 hour at ambient temperature the solution was evaporated under reduced pressure, triturated under 20 ml of cold isopropanol, and filtered to give the product. Recrystallization from isopropanol gave the title product, mp 131°-132°.

Workup

  1. customprepared
  2. customat 25°
  3. customAfter 1 hour at ambient temperature the solution was evaporated under reduced pressure
  4. customtriturated under 20 ml of cold isopropanol
  5. filtrationfiltered
  6. customto give the product
  7. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-c45f01b8d0b0407ba2d440e00c436231
Source dataset
uspto-grants-1980_09
Patent number
US04221737

Reaction notes

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