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Acetic Acid → N-tert-butylhydroxylammonium acetate

HRID 1636093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1636093
[C:1]([N:5]1C(C2C=CC=CC=2)[O:6]1)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.O1CN1.[C:22]([OH:25])(=[O:24])[CH3:23].[OH-].[Na+]>C(O)C.O.C(OCC)(=O)C>[C:22]([O-:25])(=[O:24])[CH3:23].[C:1]([NH2+:5][OH:6])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 983712-(1,1-Dimethylethyl)-3-phenyloxaziridineHCID 15817734Oxaziridine

Produkt 1

HCID 86585825N-tert-butylhydroxylammonium acetateAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-tert-Butyl-3-phenyloxaziridine (30.3 g, 98.2area %, 0.17 mol) was dissolved in ethanol (90 g). Sulphuric acid (25.7 g, 95 to 97%, 0.25 mol, 1.5 equiv.) was diluted in water (90 g) and added to the 500 ml reaction bottle. The reaction mixture was stirred at +20° C. for 20 h at which time analysis by GC showed that 5.8 area % oxaziridine remained. Leaving the reaction stirring over the weekend gave complete conversion. The solvents were evaporated and the concentrate was partitioned between water (90 g) and ethyl acetate (90 g). The organic phase was discarded and fresh ethyl acetate (150 g) and acetic acid (10.8 g, 0.18 mol, 1.1 equiv.) were added, followed by sodium hydroxide (45% aqueous solution) until the aqueous phase had approximately pH 5.5. The organic phase was then separated, filtered through K200 filter paper and concentrated giving an oil (17.3 g). This material was distilled at 20 mbar and the fractions distilling above +72° C. were collected giving a clear oil (11.5 g, 45%) that crystallized immediately. Chromatographic purity (GC): 99.5 area %

Aufarbeitung

  1. additionadded to the 500 ml reaction bottle
  2. customLeaving the reaction
  3. stirringstirring over the weekend
  4. customgave complete conversion
  5. customThe solvents were evaporated
  6. customthe concentrate was partitioned between water (90 g) and ethyl acetate (90 g)
  7. customThe organic phase was then separated
  8. filtrationfiltered through K200 filter paper
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9e81c2b5493d4dfaab5b4a860a472974
Quelldatensatz
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06512143B1

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