Acetic Anhydride → HCID 54459887, Verbindung

HRID 442693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442693
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:23][C:24](OC(C)=O)=[O:25].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[C:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:25])[CH3:23]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 9839097HCID 9839097, Verbindung

Produkt 1

HCID 54459887HCID 54459887, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 1-(4-aminophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4-(4H)-one (90 mg, 0.30 mmol) in CH2Cl2 (10 mL) was added Ac2O (0.30 mL, 3.2 mmol) and Et3N (0.60 mL, 4.3 mmol) at room temperature. The mixture was stirred at room temperature for 2 h, diluted with EtOAc (40 mL), washed with water, 2N NaOH water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography to afford the title compound as a white solid (70 mg, 0.21 mmol, 70%), mp: 177°-180° C. 1H NMR (CDCl3) 8.34 (s, 1H), 7.57 (s, 4H), 7.27 (s, 1H), 6.83 (s, 1H), 6.64 (s, 1H), 6.03 (s, 2H), 3.45 (s, 2H), 2.22 (s, 3H). Anal. calcd. for C18H15N3O4.(1/2)H2O: C, 62.42; H, 4.66; N, 12.13. Found: C, 62.60; H, 4.62; N, 11.57.

Aufarbeitung

  1. washwashed with water, 2N NaOH water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d3169367cf404b329268994ed24ddc08
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

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