Sodium Methoxide → 4-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743424
[CH3:1][O-].[Na+].C[O:5][C:6](=O)[CH:7]([CH:13]([CH3:15])C)[NH:8][S:9]([NH2:12])(=[O:11])=[O:10]>CO>[CH2:13]([CH:7]1[NH:8][S:9](=[O:11])(=[O:10])[NH:12][C:6]1=[O:5])[CH2:15][CH3:1]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 19424464N-(aminosulfonyl)-DL-valine methyl ester

Produkt 1

HCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 184.053 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of freshly prepared sodium methoxide (6.41 g, from 2.3 g of Na) in 100 ml of methanol was added to a solution of N-(aminosulfonyl)-DL-valine methyl ester (10.5 g; 0.05 mmol) in methanol (150 ml) and the resulting reaction mixture was stirred for 6 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to yield a solid residue which was crystallized from methanol/hexane to afford 16.4 g of a crude 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H R2 =isopropyl, R3 =H).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto yield a solid residue which
  6. customwas crystallized from methanol/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6c99df26eeaa46e3817f89c4d06f93f6
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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