Acetic Anhydride → HCID 9907591, Verbindung

HRID 29041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29041
[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-7a074d9672334ea2a0613f6c25f69968
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420061B2

Notizen zur Reaktion

Wird geladen…