Methyl iodide → 2-Phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743432
[CH3:1]C(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.CI>C1COCC1>[C:7]1([CH2:13][N:14]2[C:18](=[O:19])[CH:17]([CH2:20][CH2:21][CH3:22])[N:16]([CH3:1])[S:15]2(=[O:23])=[O:24])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 189222542-Phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium t-butoxide (1.05 g, 9.37 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (2.4 g, 8.95 mmol) in 25 ml of THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added methyl iodide (6.35 g, 44.73 mmol) and the resulting mixture was allowed to stir at 0° C. for 0.5 hour and at room temperature for 4 hours. The resulting mixture was quenched with saturated ammonium chloride, extracted with ethyl acetate 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 2.4 g (95%) of 2-phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazol-idin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =propyl, R3 =methyl) as an oil.

Aufarbeitung

  1. stirringto stir at 0° C. for 0.5 hour and at room temperature for 4 hours
  2. customThe resulting mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  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-50476c326f3c4cc9a5d6475c36afd464
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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