Nitromethane → 1-p-Fluorobenzyl-2-nitromethylene-pyrrolidine

HRID 426952

Reaktionsgleichung

Reaktionsgleichung von HRID 426952
S(OC)(OC)(=O)=O.[F:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=O)=[CH:11][CH:10]=1.C[O-].[Na+].[Na].[N+:26]([CH3:29])([O-:28])=[O:27]>O.CO>[F:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[CH:29][N+:26]([O-:28])=[O:27])=[CH:11][CH:10]=1

Komponenten

8

Edukt 5

HCID 6375NitromethaneHCID 6497Dimethyl SulfateHCID 30454462-Pyrrolidinone, 1-((4-fluorophenyl)methyl)-HCID 5360545SodiumHCID 10942334Sodium Methoxide

Produkt 1

HCID 540091111-p-Fluorobenzyl-2-nitromethylene-pyrrolidineAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

26.1 g (0.207 mol) of dimethyl sulphate are added to 40 g (0.207 mol) of 1-p-fluorobenzyl-pyrrolidin-2-one and the mixture is heated to 60° for 4 hours. It is then cooled and a solution of sodium methylate prepared from 4.75 g (0.207 gram atom) of sodium and 100 ml of methanol is introduced slowly, at 0°. When the addition is complete, the mixture is stirred for 30 minutes at 50° C. and again cooled to 0°, and 18.9 g (0.31 mol) of nitromethane are added dropwise whilst continuing the stirring. The reaction mixture is left at ambient temperature for 12 hours and is then heated to 50° for 2 hours. It is cooled, and poured into 500 ml of water, which are then extracted with chloroform. The organic layer is now separated off, washed with water and dried over magnesium sulphate, and the solvent is driven off. The residual product is washed with ether and recrystallised from ethanol. 27 g (55.2% yield) of 1-p-fluorobenzyl-2-nitromethylene-pyrrolidine are thus collected in the form of light yellow crystals melting at 108.5°-109°.

Aufarbeitung

  1. temperaturethe mixture is heated to 60° for 4 hours
  2. temperatureIt is then cooled
  3. additionis introduced slowly, at 0°
  4. additionWhen the addition
  5. temperatureagain cooled to 0°
  6. waitThe reaction mixture is left at ambient temperature for 12 hours
  7. temperatureis then heated to 50° for 2 hours
  8. temperatureIt is cooled
  9. extractionare then extracted with chloroform
  10. customThe organic layer is now separated off
  11. washwashed with water
  12. dry with materialdried over magnesium sulphate
  13. washThe residual product is washed with ether
  14. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d0cfedf70e894672bed7d8a50dcaf016
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172143

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