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

HRID 2050367Notes

Reaction equation

HRID 2050367 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. 841,353], 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-d12cdef597744dd493c2b230b17dab79
Source dataset
uspto-grants-1980_04
Patent number
US04200760

Reaction notes

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