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

HRID 75262

반응식

HRID 75262 반응식
[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

참가 물질

5

반응물 2

HCID 24408BromineHCID 110322973-Methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one2회

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 1118Sulfuric Acid용매

실험 절차

To a stirred solution of 131 (66.5 g, 265 m mol) 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, 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 (45), 285 (60), 205 (25), 77 (49).

후처리

  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

출처 및 근거

ORD 기록
ord-cdc748ea319c451e82f9b532bb976812
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835424B2

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