Triethylamine → 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine

HRID 1018473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018473
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl.[CH3:23][CH:24]1[CH:29]=[C:28]([CH3:30])[CH:27]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[CH:33][CH:32]=2)[O:26][NH:25]1>ClCCl>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([N:25]2[CH:24]([CH3:23])[CH:29]=[C:28]([CH3:30])[CH:27]([C:31]3[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH3:39])=[CH:35][CH:36]=3)[O:26]2)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 184015323,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of 4-N-acetylsulphanilyl chloride (1.14 g, 4.9 mmol) and triethylamine (0.82 g, 8.15 mmol) in dichloromethane (15 ml) was added a solution of 3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine hydrochloride (0.88 g, 3.26 mmol) in dichloromethane (15 ml). The resulting solution was stirred at room temperature for 8 h then washed with water three times, aqueous sodium hydroxide (2M), water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to a foam. The crude product was purified on flash silica eluting with ethylacetate-hexane (3:2) to give 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-3,5-dimethyl-6-(4-ethoxyphenyl)-2H-1,2-oxazine as a white foam. 1H NMR (CDCl3) δ 1.41(9H, m), 2.14(3H, s), 4.01(2H, q), 4.43(1H, m), 5.17(1H, s), 5.66(1H, d), 6.79(2H, d), 7.11(2H, d), 7.60(2H, d), 7.79(2H, d), 7.89(1H, bs).

Aufarbeitung

  1. washthen washed with water three times, aqueous sodium hydroxide (2M), water and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to a foam
  5. customThe crude product was purified on flash silica eluting with ethylacetate-hexane (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-26c068e13d2a4eb794407c4b503c756e
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06482824B1

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