P-Toluenesulfonamide → 1,3-Dimethyl-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole

HRID 1769085

Reaktionsgleichung

Reaktionsgleichung von HRID 1769085
Cl[CH2:2][C:3]1[C:7]([CH2:8]Cl)=[C:6]([CH3:10])[S:5][C:4]=1[CH3:11].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:4]1[S:5][C:6]([CH3:10])=[C:7]2[CH2:8][N:21]([S:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=3)(=[O:19])=[O:20])[CH2:2][C:3]=12

Komponenten

5

Edukt 3

HCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 2883993,4-Bis(chloromethyl)-2,5-dimethylthiophene

Produkt 1

HCID 189470571,3-Dimethyl-5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrroleAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 10 g (0.048 mol) of 3,4-bis(chloromethyl)-2,5-dimethylthiophene and 8.22 g of p-toluenesulphonamide in 600 ml of dry dimethylformamide is added dropwise, over 6 h, to a stirred suspension, heated to 100°-110° C., of 180 g of potassium carbonate in 900 ml of dimethylformamide. After the end of the addition, the mixture is maintained at the same temperature for 30 min, and then filtered. The solid is washed with dimethylformamide. The filtrate is concentrated under vacuum, and the residue is treated with 100 ml of ethanol, and filtered. The solid residue remaining is washed with ethanol and dried. 9.39 g of product are obtained. Melting point: 163°-164° C.

Aufarbeitung

  1. additionAfter the end of the addition
  2. temperaturethe mixture is maintained at the same temperature for 30 min
  3. filtrationfiltered
  4. washThe solid is washed with dimethylformamide
  5. concentrationThe filtrate is concentrated under vacuum
  6. additionthe residue is treated with 100 ml of ethanol
  7. filtrationfiltered
  8. washThe solid residue remaining is washed with ethanol
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-32ddc447f8a04f45a562d00df4e39c31
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380742

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