Acetic Anhydride → HCID 9907591, Verbindung

HRID 2414793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414793
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:15][C:16]1[O:20][N:19]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[C:17]=1[C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH2:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>O1CCCC1>[F:27][C:23]1[CH:22]=[C:21]([C:18]2[C:17]([C:28]3[CH:29]=[CH:30][C:31]([S:34]([NH:37][C:1](=[O:3])[CH3:2])(=[O:36])=[O:35])=[CH:32][CH:33]=3)=[C:16]([CH3:15])[O:20][N:19]=2)[CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 226435854-[5-Methyl-3-(3-fluorophenyl)isoxazol-4-yl]benzenesulfonamide

Produkt 1

HCID 9907591HCID 9907591, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Acetic anhydride (1.01 g, 9.39 mmol) and triethylamine (0.401 g, 3.97 mmol) were added to a solution of 4-[5-methyl-3-(3-fluorophenyl)isoxazol-4-yl]benzenesulfonamide (1.10 g, 3.31 mmol) and N,N-dimethylpyridine (0.202 g) in dry tetrahydrofuran. After stirring for 18 hours at room temperature, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate, washed successively with 1N hydrochloric acid and brine, dried over anhydrous MgSO4 and concentrated to afford 1.0 g (81%) of the desired product as a crystalline product: mp 144-145° C. 1H NMR (CDCl3) 8.00 (d, 2H, J=7.3 Hz), 7.30-7.27 (m, 4H), 7.10-7.06 (m, 3H), 2.46 (s, 3H), 1.99 (s, 3H). Anal. Calc'd for C18H15FN2O4S: C, 57.75; H, 4.04; N, 7.48. Found: C, 57.84; H, 4.06; N, 7.49.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with 1N hydrochloric acid and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2690f37924124d728eb1b23c54149f20
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06815460B2

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