1,1-Bis(methylthio)-2-nitroethylene → 3-(3-pyridylmethyl)2-nitromethylenetetrahydro-2H-1,3-thiazine

HRID 487916Notes

Reaction equation

HRID 487916 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][SH:12])[CH:2]=1.[N+:13]([CH:16]=[C:17](SC)SC)([O-:15])=[O:14]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][S:12][C:17]2=[CH:16][N+:13]([O-:15])=[O:14])[CH:2]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 13752794N-(3-pyridylmethyl)3-aminopropanethiol

Product 1

HCID 539788653-(3-pyridylmethyl)2-nitromethylenetetrahydro-2H-1,3-thiazineYield 48.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(3-pyridylmethyl)3-aminopropanethiol (1.8 g), 1-nitro-2,2-bis(methylthio)ethylene (1.7 g) and ethanol (40 ml) was heated under reflux for 5 hours under a nitrogen stream. After the reaction, about 2/3 by volume 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-(3-pyridylmethyl)2-nitromethylenetetrahydro-2H-1,3-thiazine (1.2 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours under a nitrogen stream
  3. customAfter the reaction
  4. distillationabout 2/3 by volume 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-d1b16d8bc7ee45929f376d0822f4cfb6
Source dataset
uspto-grants-1994_03
Patent number
US05298507

Reaction notes

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