Benzyl Bromide → 2-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743431
[CH2:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])[CH2:2][CH3:3].[C:12]1([CH2:18]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([CH2:18][N:6]2[C:5](=[O:11])[CH:4]([CH2:1][CH2:2][CH3:3])[NH:8][S:7]2(=[O:9])=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 7498Benzyl BromideHCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Produkt 1

HCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5.0 g, 28.25 mmol) suspended in 150 ml of toluene was added phenylmethyl bromide (5.32 g, 31.03 mmol) and tetrabutylammonium bromide (0.9 g, 0.28 mmol). The resulting mixture was refluxed for 19 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to afford 2.97 g (39%) of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IX: R1 =H; R2 =propyl) as a solid, m.p., 63.5°-65.5° C.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 19 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4c7f8976d9fd47fba04dd21f336b7899
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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