Iodoethane → 2-Phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743442
[CH3:1][C:2](C)([O-])C.[K+].[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH2:20][CH2:21][CH3:22])[NH:16][S:15]2(=[O:24])=[O:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(I)C>C1COCC1>[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH2:20][CH2:21][CH3:22])[N:16]([CH2:1][CH3:2])[S:15]2(=[O:23])=[O:24])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 194244172-Phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 1.139,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium t-butoxide (2.3 g, 2.05 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (5 g, 1.56 mmol) in 100 ml of THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added ethyl iodide (11.64 g, 7.46 mmol) at 0° C. and the resulting mixture was allowed to stir at room temperature for 40 hours. The resulting mixture was quenched with brine, extracted with ethyl acetate (150 ml) and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 5.27 g of 2-phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =propyl; R3 =ethyl) as an oil.

Aufarbeitung

  1. stirringto stir at room temperature for 40 hours
  2. customThe resulting mixture was quenched with brine
  3. extractionextracted with ethyl acetate (150 ml)
  4. washthe organic layer was washed with brine
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c20b6a07ce154e8280751d5592561306
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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