Ethyl Acetate → 7-Bromo-3-methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

HRID 75253

Reaktionsgleichung

Reaktionsgleichung von HRID 75253
[K+].[Br-].N1C2C=CC=CC=2C=C[CH:5]=N1.FC(F)(F)COC(C1N=C[N:23]2[C:29]3[CH:30]=[CH:31][C:32]([Br:34])=[CH:33][C:28]=3[C:27]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3F)=[N:26]CC=12)=O.CCO[C:47]([CH3:49])=[O:48]>>[Br:34][C:32]1[CH:31]=[CH:30][C:29]2[NH:23][C:47](=[O:48])[CH:49]([CH3:5])[N:26]=[C:27]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:28]=2[CH:33]=1

Komponenten

5

Edukt 4

HCID 8857Ethyl AcetateHCID 134664Benzodiazepine3×HCID 253877Potassium BromideHCID 21930955HCID 21930955, Verbindung

Produkt 1

HCID 6255777-Bromo-3-methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

Versuchsvorschrift

To a stirred solution of 110 (66.5 g, 265 mmol) in glacial acetic acid (400 mL), sulfuric acid (80 mL) was added to the solution. Bromine (28 mL, 530 mmol) dissolved in acetic acid (150 mL) was added dropwise into the mixture. The reaction mixture was allowed to stir until NMR spectroscopy indicated that all of the starting material 110 had been consumed. The solution was concentrated under reduced pressure and then neutralized by addition of 1N NaOH solution and then extracted with EtOAc. The crude product 111 was purified by recrystallization from CH2Cl2 to afford 5 (70.4 g, 81%). mp 210-212° C.; IR (KBr, cm−1) 2931, 1692, 1603, 1563, 1475, 1445, 1375, 1259, 1235, 1130, 1090; 1H NMR (CDCl3) δ 9.36 (s, 1 H), 7.63 (dd, J=2.22, 8.58 Hz, 1 H), 7.54-7.39 (m, 6 H), 7.12 (d, J=8.61 1 H), 3.76 (q, J=6.3 Hz, 1 H), 1.76 (d, J=6.45 Hz, 3 H). MS (EI) m/e (relative intensity) 330 (M++1, 21), 329 (M+, 50), 328 (22), 327 (48), 289 (44), 288 (46), 287 (100), 286 (49), 285 (60), 205 (25), 77 (49); [α]26D=313.1 (c 0.34, EtOAc).

Quellen und Nachweise

ORD-Eintrag
ord-023a8cd96a734422b8ac66b128d7ad31
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835424B2

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