N-bromobutanimide → 1-Bromo-4-chloro-7,8-dimethylimidazo[1,2-A]quinoxaline

HRID 1025480노트

반응식

HRID 1025480 반응식
[Cl:1][C:2]1[C:3]2[N:4]([CH:14]=[CH:15][N:16]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([CH3:12])=[C:7]([CH3:13])[CH:6]=2.C1C(=O)N([Br:24])C(=O)C1>C1COCC1.CN1C(=O)CCC1>[Br:24][C:14]1[N:4]2[C:5]3[C:10]([N:11]=[C:2]([Cl:1])[C:3]2=[N:16][CH:15]=1)=[CH:9][C:8]([CH3:12])=[C:7]([CH3:13])[CH:6]=3

참가 물질

4

반응물 2

HCID 67184N-bromobutanimide2회HCID 866653244-Chloro-7,8-dimethyl-imidazo[1,2-a]quinoxaline

생성물 1

HCID 717416381-Bromo-4-chloro-7,8-dimethylimidazo[1,2-A]quinoxaline수율 81.1%

시약·촉매·용매 1

HCID 22156051tetrahydrofuran N-methylpyrrolidinone용매

실험 절차

To a stirred suspension of 4-chloro-7,8-dimethyl-imidazo[1,2-a]quinoxaline (32.2 g, 0.148 mot) in THF/NMP 2:1 (312 mL) was added NBS (26.3 g, 0.148 mot) in one portion at room temperature. After stirred for 18 h, additional NBS (13.1 g, 0.074 mot) was added and the mixture was stirred for additional 2 h at room temperature. After removal of the THF portion of the organic phase by vacuum evaporation, water was added (520 mL). The precipitate was filtered and the residue was washed with water, diethyl ether and dried to give 35 g of the title compound. 1H-NMR (300 MHz, d6-DMSO): δ=8.54 (1H, s), 7.75 (1H, s), 7.40 (1H, s), 2.20 (6H, s) ppm.

후처리

  1. stirringthe mixture was stirred for additional 2 h at room temperature
  2. customAfter removal of the THF portion of the organic phase
  3. customby vacuum evaporation, water
  4. additionwas added (520 mL)
  5. filtrationThe precipitate was filtered
  6. washthe residue was washed with water, diethyl ether
  7. customdried

출처 및 근거

ORD 기록
ord-0ebe3b7a866c4e49a7651e9a05e4bdce
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729082B2

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