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

HRID 1435814

Reaktionsgleichung

Reaktionsgleichung von HRID 1435814
[CH3:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:3]1.[Br:20]Br>C(O)(=O)C.S(=O)(=O)(O)O>[Br:20][C:12]1[CH:11]=[CH:10][C:6]2[NH:7][C:8](=[O:9])[CH:2]([CH3:1])[N:3]=[C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]=2[CH:13]=1

Komponenten

5

Edukt 2

HCID 24408BromineHCID 110322973-Methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one2×

Produkt 1

HCID 6255777-Bromo-3-methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-oneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of 131 (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 analysis by NMR spectroscopy indicated that all of the starting material 131 had been consumed. The solution was concentrated under reduced pressure and then brought to pH 7 by addition of 1N aq NaOH solution and then extracted with EtOAc. The crude product 132 was purified by recrystallization from CH2Cl2 to afford 132 (68.66 g, 79%). 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, 1H), 7.63 (dd, J=2.22, 8.58 Hz, 1H), 7.54-7.39 (m, 6H), 7.12 (d, J=8.611H), 3.76 (q, J=6.3 Hz, 1H), 1.76 (d, J=6.45 Hz, 3H). MS (EI) m/e (relative intensity) 330 (M++1, 21), 329 (M+, 50), 328 (22), 327 (48), 289 (44), 288 (46), 287 (100), 286 (45), 285 (60) 205 (25), 77 (49).

Aufarbeitung

  1. additionwas added dropwise into the mixture
  2. customhad been consumed
  3. concentrationThe solution was concentrated under reduced pressure
  4. additionbrought to pH 7 by addition of 1N aq NaOH solution
  5. extractionextracted with EtOAc
  6. customThe crude product 132 was purified by recrystallization from CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-df8536de0a054f719e5a9dbf892de850
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618958B2

Verknüpfte Notizen

Wird geladen…