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

HRID 127321Notes

Reaction equation

HRID 127321 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 liters). The solution was heated to boiling and 0.7 liters of solvent were distilled off. The cooled solution was washed with 2N 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 2N 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-17a4d88615b048d4abf5d8d094c5253d
Source dataset
uspto-grants-1981_03
Patent number
US04255440

Reaction notes

Loading…