Methyl fluorosulfate → N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate

HRID 1649046

Reaktionsgleichung

Reaktionsgleichung von HRID 1649046
[CH3:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=O.FS(OC)(=O)=O.[C:14]1([NH:20][C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[NH:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C(Cl)Cl.C(O)(C)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH3:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=[N:22][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[N:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

8

Edukt 5

HCID 9870Methyl fluorosulfateHCID 14798Sodium HydroxideHCID 298312-Oxazolidinone, 3-methyl-HCID 444972Fumaric AcidHCID 178511988HCID 178511988, Verbindung

Produkt 1

HCID 70510611N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-methyloxazolidin-2-one, 2.02 g (0.02 mole), in dry methylene chloride under dry nitrogen is added 2.28 g (0.02 mole) of methyl fluorosulfonate in one portion. After stirring 3 hrs, 0.02 mole of N-phenyl-1-pyrrolidinecarboximidamide free base in dry methylene chloride is added. After stirring at room temperature overnight, the solution is shaken with excess cold 3 N NaOH. The organic layer is separated and dried over K2CO3, filtered, and the solvent removed in vacuo to afford the crude base. Addition of an equimolar amount of fumaric acid to a solution of the free base in isopropanol, followed by recrystallization from isopropanol/ether affords pure N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate; m.p. 160°-162° C.

Aufarbeitung

  1. stirringAfter stirring at room temperature overnight
  2. customThe organic layer is separated
  3. dry with materialdried over K2CO3
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto afford the crude base
  7. customfollowed by recrystallization from isopropanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-e962d691496846a3a53882cbbe5133fd
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04414211

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