Water → N-hydroxy-N-(3-benzo[b]thien-2-ylprop-2-enyl) acetamide

HRID 2351465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2351465
O1CCCCC1[O:7][NH:8][CH2:9][CH:10]=[CH:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1.[O:21]1CCC[CH2:23][CH:22]1NO.S1C=C(C(Br)C=C)C2C=CC=CC1=2.O>CN(C=O)C>[OH:7][N:8]([CH2:9][CH:10]=[CH:11][C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)[C:22](=[O:21])[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 13168123Tetrahydropyranyl hydroxylamineHCID 198463353-Benzo[b]thienylbromoprop-2-eneHCID 86743434O-Tetrahydropyranyl-3-benzo[b]thien-2-ylprop-2-enyl hydroxylamine

Produkt 1

HCID 24103629N-hydroxy-N-(3-benzo[b]thien-2-ylprop-2-enyl) acetamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

O-Tetrahydropyranyl-3-benzo[b]thien-2-ylprop-2-enyl hydroxylamine. Tetrahydropyranylhydroxyl amine (0.51 g, 4.34 mmole) in DMF (10 mL) was added to a solution of 3-benzo[b]thienylbromoprop-2-ene (0.50 g, 1.98 mmole) in DMF (10 mL). After being allowed to stir for two hours the reaction was poured into water and extracted with ether. The organic layer was washed with NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated. The residue was chromatographed on silica gel eluting with 40% ether in hexanes to give the desired product as a yellow oil (66%).

Aufarbeitung

  1. extractionextracted with ether
  2. washThe organic layer was washed with NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with 40% ether in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-18a37d57f339492d9e98a2d2ddc0525b
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04873259

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