Potassium Hydroxide → 2-(4-aminobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

HRID 1018476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018476
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:19]([CH3:20])[CH:18]=[C:17]([CH3:21])[CH:16]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=3)[O:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[OH-].[K+]>CO.ClCCl>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[CH:19]([CH3:20])[CH:18]=[C:17]([CH3:21])[CH:16]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH3:30])=[CH:26][CH:27]=3)[O:15]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 98455822-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

Produkt 1

HCID 117736522-(4-aminobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 2-(4-acetamidobenzenesulphonyl)-3, 6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl) -2H-1,2-oxazine (0.153 g) and powdered potassium hydroxide (40mg) in methanol (5 ml) was-heated under reflux for 24 h. The cooled mixture was diluted with dichloromethane and the solution washed with water. The dichloromethane solution was separated, dried over magnesium sulphate, filtered and evaporated to dryness. The residual oil was purified by chromatography on silica using ethyl acetate:n-hexane 3:2 as eluant to give 2-(4-aminobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine as a colourless foam. 1H NMR (CDCl3) δ 1.44(9H, m), 4.02(2H, q), 4.13(2H, br s), 4.44 (1H, m), 5.02(1H, br s), 5.70(1H, m), 6.61(2H, d), 6.83(2H, d), 7.13(2H, d), 7.65(2H, d).

Aufarbeitung

  1. temperaturewas-heated
  2. temperatureunder reflux for 24 h
  3. washthe solution washed with water
  4. customThe dichloromethane solution was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residual oil was purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-d47fad984ca1487092ab21090d320441
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06482824B1

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