Methylamine → N-Methyl-1-(methylsulfanyl)-2-nitroethan-1-amine

HRID 426488Notes

Reaction equation

HRID 426488 reaction equation
[CH3:1][NH2:2].C(O)C.C(Cl)CCl.[CH3:10][S:11][C:12](SC)=[CH:13][N+:14]([O-:16])=[O:15]>C(Cl)CCl>[CH3:1][NH:2][CH:12]([S:11][CH3:10])[CH2:13][N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 229016121,2-Dichloroethane ethanol

Product 1

HCID 15788612N-Methyl-1-(methylsulfanyl)-2-nitroethan-1-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of methylamine in ethanol/ethylenedichloride (112.5 ml of 33% ethanolic methylamine in 0.8 liters of ethylene dichloride; 0.94 mole) was added over 51/2 hr at 70° to a stirred solution of 1,1-bismethylthio-2-nitroethene (99.0 g, 0.6 mole) in ethylene dichloride (1.5 litres). The solution was heated to boiling and 0.7 liters of solvent were distilled off. The cooled solution was washed with 2 N hydrochloric acid (0.25 liters), then with brine (0.25 liters). The solvent was removed and the residue crystallised from isopropyl acetate (0.5 liters), treating the hot solution with charcoal (10.0 g). The product (35.0 g) formed yellow prisms, m.p. 114°.

Workup

  1. temperatureThe solution was heated
  2. distillation0.7 liters of solvent were distilled off
  3. washThe cooled solution was washed with 2 N hydrochloric acid (0.25 liters)
  4. customThe solvent was removed
  5. customthe residue crystallised from isopropyl acetate (0.5 liters)
  6. additiontreating the hot solution with charcoal (10.0 g)

Sources & evidence

ORD record
ord-398c82f5d14c448492bab9c8b502c38c
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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