Methyl iodide → 6-(3-Bromo-5-fluorophenyl)-1,4,4-trimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

HRID 413147노트

반응식

HRID 413147 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:21]=[CH:20][C:12]3[NH:13][C:14](=[O:19])[O:15][C:16]([CH3:18])([CH3:17])[C:11]=3[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].I[CH3:25].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]([CH3:25])[C:14](=[O:19])[O:15][C:16]([CH3:17])([CH3:18])[C:11]=3[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98098756-(3-Bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one

생성물 1

HCID 102701136-(3-Bromo-5-fluorophenyl)-1,4,4-trimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one (0.34 g, 0.99 mmol) in dry DMF (10 mL) was added under nitrogen at room temperature sodium hydride (80 mg, 2.0 mmol) in one portion. The mixture was stirred at ambient temperature for 30 minutes, treated with iodomethane (1 mL, excess), and stirred for 2 hours. To the reaction mixture was added a cold saturated ammonium chloride solution (30 mL) and the white precipitate obtained was collected on a filter, washed with the distilled water to afford the title compound as a white solid (0.31 g, 87%): mp 157-158° C.; 1H-NMR (DMSO-d6) δ7.83 (s, 1H), 7.76 (dd, 1H, J=8.5, 2.0 Hz), 7.67 (m, 2H), 7.53 (dt, 1H, J=8.3, 1.9 Hz), 7.18 (d, 1H, J=8.5 Hz), 3.33 (s, 3H), 1.67 (s, 6H); 19F-NMR (DMSO-d6) δ−111.01 (m, 1F); MS (APCI) m/z 364 ([M+H]+, 96%), 366 ([M+H]+, 100%).

후처리

  1. stirringstirred for 2 hours
  2. customthe white precipitate obtained
  3. customwas collected on a filter
  4. washwashed with the distilled water

출처 및 근거

ORD 기록
ord-1a52591cac174a09b3a290e618fba9f8
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566358B2

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