Formic Acid → Ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate

HRID 364493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 364493
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH2:34][CH:35]=[CH2:36])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O>O1CCCC1>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH2:34][CH:35]=[CH2:36])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 54525939Ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate

Produkt 1

HCID 54209614Ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetateAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 8.7 g.). 50% formic acid (42.5 ml.) and tetrahydrofuran (42.5 ml.) was stirred at 60° C. for 40 minutes. After concentrating the resultant solution in vacuo, the residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. After concentrating the resultant solution in vacuo, the residue was subjected to column chromatography on silica gel with benzene and ethyl acetate in turn, to give ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 3.7 g.), mp. 102° to 104° C.

Aufarbeitung

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with an aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  5. concentrationAfter concentrating the resultant solution in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9421975d050540369808e2bb877c56aa
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604456

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