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

HRID 743425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743425
[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 mmol) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.83 g, 43 mmol) and tetrabutylammonium bromide (1.26 g, 3.93 mmol). 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-7091787311fc43e8b1b57e5c95b7bbac
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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