1,1-Bis(methylthio)-2-nitroethylene → HCID 53964092, compound

HRID 1590667Notes

Reaction equation

HRID 1590667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][SH:13])=[CH:4][N:3]=1.[N+:14]([CH:17]=[C:18](SC)SC)([O-:16])=[O:15]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][S:13][C:18]2=[CH:17][N+:14]([O-:16])=[O:15])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 13752791HCID 13752791, compound

Product 1

HCID 53964092HCID 53964092, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2-chloro-5-pyridylmethyl)3-aminopropanethiol (4.3 g), 1-nitro-2,2-bis(methylthio)ethylene (3.3 g) and ethanol (40 ml) was heated under reflux for 10 hours in a stream of nitrogen. After the reaction, about 2/3 of ethanol was distilled off under reduced pressure. Ether was added little by little to the reaction mixture to precipitate crystals. The crystals were collected by filtration, and washed with a mixture of ethanol and ether to give the desired 3-(2-chloro-5-pyridylmethyl)-2-nitromethylenetetrahydro-2H-1,3-thiazine (1.3 g) as yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours in a stream of nitrogen
  3. customAfter the reaction
  4. distillationabout 2/3 of ethanol was distilled off under reduced pressure
  5. additionEther was added little by little to the reaction mixture
  6. customto precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. washwashed with a mixture of ethanol and ether

Sources & evidence

ORD record
ord-568dd7045c324bbe91b5f7676deb478f
Source dataset
uspto-grants-1993_04
Patent number
US05204360

Reaction notes

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