Acetaldehyde → 4H-Pyrrolo2,1-d-1,3,5-dithiazine, tetrahydro-2,4-dimethyl-, 2S-(2alpha,4alpha,8abeta)-

HRID 1905775

Reaction equation

HRID 1905775 reaction equation
[CH:1](=O)[CH3:2].[N:4]1[CH2:8][CH2:7][CH2:6][CH:5]=1.[SH2:9].[S:10]([O-])([O-])(=O)=O.[Mg+2].CCO[CH2:19][CH3:20]>>[CH3:20][CH:19]1[S:10][CH:5]2[CH2:6][CH2:7][CH2:8][N:4]2[CH:1]([CH3:2])[S:9]1

Participants

6

Reactant 5

HCID 177AcetaldehydeHCID 402Hydrogen SulfideHCID 3283Diethyl EtherHCID 24083Sulfuric acid magnesium salt (1:1)HCID 798031-Pyrroline

Product 1

HCID 5290684H-Pyrrolo2,1-d-1,3,5-dithiazine, tetrahydro-2,4-dimethyl-, 2S-(2alpha,4alpha,8abeta)-

Procedure

44 g (1 mol) of acetaldehyde are added dropwise to a solution of 34.5 g (0.5 mol) of 1-pyrroline in 150 ml of ether. Hydrogen sulphide is then passed into the reaction mixture, while the latter is cooled with ice, until saturation is reached. After 10 g of magnesium sulphate have been added, the reaction mixture is kept at room temperature for 15 hours. When the ether has been removed by distillation, the residue is fractionally distilled. 43 g of 2,4-dimethyltetrahydropyrrolo[2.1-d]-[1,3,5]-dithiazine (boiling point at 6 mbar: 105° C.) are obtained.

Workup

  1. temperatureis cooled with ice, until saturation
  2. customWhen the ether has been removed by distillation
  3. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-4e8523f985ea483e801011d304b28013
Source dataset
uspto-grants-1987_03
Patent number
US04647662

Linked notes

Loading…