Triethylamine → Ethyl O-Mesitylsulfonylacetohydroxamate

HRID 2272823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272823
[OH:1]/[N:2]=[C:3](/[O:5][CH2:6][CH3:7])\[CH3:4].C(N(CC)CC)C.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24](Cl)(=[O:26])=[O:25]>CN(C=O)C>[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24]([O:1]/[N:2]=[C:3](/[O:5][CH2:6][CH3:7])\[CH3:4])(=[O:25])=[O:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 5363167Ethyl N-hydroxyacetimidate

Produkt 1

HCID 6282444Ethyl O-MesitylsulfonylacetohydroxamateAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ethyl (1E)-N-hydroxyethanimidate (8.4 g, 81.5 mmol) in DMF (20 mL) is added triethylamine (12 mL, 86.24 mmol) and the mixture is stirred for 20 minutes. 2,4,6-Trimethylbenzene-1-sulfonyl chloride (20 g, 81.5 mmol) is added and the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is quenched with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts are dried over sodium sulphate, filtered, and evaporated to dryness to give the title compound as white solid (15 g, 64%). The crude material is used without further purification.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at room temperature for 16 hours
  2. customThe reaction mixture is quenched with water (100 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic extracts are dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ac5865e2dcdc4a608ac1c14297bbddea
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120793B2

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