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p-Toluenesulfonic acid monohydrate → 3-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione

HRID 922134
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922134
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:36])=[C:18]([C:20]2[C:21](=[O:35])[NH:22][C:23]3([C:33]=2[OH:34])[CH2:32][CH2:31][C:26]2(OCC[O:27]2)[CH2:25][CH2:24]3)[CH:19]=1>CC(C)=O.O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:36])=[C:18]([C:20]2[C:21](=[O:35])[NH:22][C:23]3([CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32]3)[C:33]=2[OH:34])[CH:19]=1
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Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 6827112611-(5-Bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one

Produkt 1

HCID 673756183-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962
Water
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

192 mg (1.01 mmol) of 4-toluenesulphonic acid monohydrate were added to 2.49 g (6.32 mmol) of 11-(5-bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (Example 38A) in 26 ml of acetone and 13 ml of water. The reaction mixture was stirred at 80° C. overnight. For work-up, the cold reaction mixture was diluted with water and acetone was removed on a rotary evaporator. The precipitated crude product was extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. Drying gave 1.97 g (89% of theory) of the title compound.

Aufarbeitung

  1. customFor work-up, the cold reaction mixture
  2. customwas removed on a rotary evaporator
  3. customThe precipitated crude product
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customDrying

Quellen und Nachweise

ORD-Eintrag
ord-ac91620567144419936d7f7c1802a9fd
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278925B2

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