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Triethylamine → 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime

HRID 1981374
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1981374
C(N(CC)CC)C.[N:8](=[C:10]1[S:14][C:13]([CH3:16])([CH3:15])[N:12]=[C:11]1[CH3:17])[OH:9].[CH3:18][N:19]([S:23][N:24]([CH3:28])[C:25](F)=[O:26])[C:20]([F:22])=[O:21]>C1(C)C=CC=CC=1>[CH3:18][N:19]([S:23][N:24]([CH3:28])[C:25]([O:9][N:8]=[C:10]1[S:14][C:13]([CH3:16])([CH3:15])[N:12]=[C:11]1[CH3:17])=[O:26])[C:20]([F:22])=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12897270bis-(N-methyl-N-fluorocarbonylamino)sulfideHCID 1362290545-Oxo-2,2,4-trimethyl-3-thiazoline oxime

Produkt 1

HCID 538867305-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

8.3 ml of triethylamine are added dropwise to a suspension of 8.59 g of 5-oxo-2,2,4-trimethyl-3-thiazoline oxime in a solution of 10.0 g of bis-(N-methyl-N-fluorocarbonylamino)sulfide in 100 ml of absolute toluene, cooled to -50° C. The resulting clear solution is allowed to warm slowly to 0° C. during 11/2 hours, during which time a crystalline product is precipitated. The reaction mixture is poured into ice-cold brine and extracted with ethyl acetate. After drying the organic phase over anhydrous sodium sulfate and evaporating it, the resulting residue is purified by chromatography on silica gel (eluent:ethyl acetate/n-hexane 1:1). Crystallization from ethyl acetate/n-hexane yields 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime, m.p. 77°-79° C.

Aufarbeitung

  1. temperatureto warm slowly to 0° C. during 11/2 hours
  2. customduring which time a crystalline product is precipitated
  3. additionThe reaction mixture is poured into ice-cold brine
  4. extractionextracted with ethyl acetate
  5. dry with materialAfter drying the organic phase over anhydrous sodium sulfate
  6. customevaporating it
  7. customthe resulting residue is purified by chromatography on silica gel (eluent:ethyl acetate/n-hexane 1:1)
  8. customCrystallization from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2f5c88dbb8f24077b1f30030dd6ef7ad
Quelldatensatz
uspto-grants-1985_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04514566

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