Toluene → 2-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396771
[CH:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])(C)[CH3:2].[C:12]1([S:18][CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:21]1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18][CH2:19][N:6]2[C:5](=[O:11])[CH:4]([CH2:1][CH2:2][CH3:21])[NH:8][S:7]2(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 81623Chloromethyl phenyl sulphideHCID 194244514-Isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Produkt 1

HCID 194244652-Phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74236Tetrabutylammonium BromideKatalysator

Versuchsvorschrift

To a mixture of 4-isopropyl-1,2, 5-thiadiazolidin-3-one 1, 1-dioxide (7.0 g, 39.32 retool) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.83 g, 43 mmol) and tetrabutylammonium bromide (1.26 g, 3.93 retool). The resulting mixture was refluxed for 17 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 5.2 g of 2-phenylthiomethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =isopropyl; R3 =H) .

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 17 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d863fc26596d458b8650799e2497cdad
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05494925

Notizen zur Reaktion

Wird geladen…