Hydroxyamine hydrochloride → N-hydroxy-2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetamide

HRID 742054

Reaktionsgleichung

Reaktionsgleichung von HRID 742054
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:18][C:19](OCC)=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[NH2:29][OH:30].C[O-].[Na+].[Na]>CO>[OH:30][NH:29][C:19](=[O:20])[CH2:18][N:17]([S:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:9][CH:10]=1)(=[O:16])=[O:15])[CH2:24][CH:25]([CH3:27])[CH3:26]

Komponenten

6

Edukt 4

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10834775Ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetateHCID 10942334Sodium Methoxide

Produkt 1

HCID 10738924N-hydroxy-2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetate (1.22 g, 3.05 mmol) is dissolved in methanol (15 mL). To this solution is added hydroxylamine hydrochloride (0.43 g, 6.11 mmol), followed by the addition of sodium methoxide, freshly prepared from sodium (0.35 g, 15.3 mmol) dissolved in methanol (5 mL). The reaction is stirred for 36 hours at room temperature. The reaction is worked up by partitioning between dilute hydrochloric acid (pH=~3) and ethyl acetate. The aqueous phase is extracted well with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is crystallized from hexane/ethyl acetate and collected by filtration to give N-hydroxy-2-[[4-hexyloxybenzenesulfonyl](isobutyl)-amino]acetamide, m.p. 108°-110° C.

Aufarbeitung

  1. customby partitioning between dilute hydrochloric acid (pH=~3) and ethyl acetate
  2. extractionThe aqueous phase is extracted well with ethyl acetate
  3. dry with materialthe combined organic layers are dried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe product is crystallized from hexane/ethyl acetate
  6. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-477f3476ce344ca290a646b1cb740e71
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552419

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