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Sodium Carbonate → N-[2-(6-Bromo-2-pyrazinyl)-4-methylphenyl]-2,2-dimethyl-propanamide

HRID 1780588
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HRID 1780588 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[BrH:28].C(O)(=O)C>>[Br:28][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1
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참가 물질

4

반응물 3

HCID 10340Sodium CarbonateHCID 19047050N-[2-(6-Chloro-2-pyrazinyl)-4-methylphenyl]-2,2-dimethylpropanamideHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

생성물 1

HCID 19047047N-[2-(6-Bromo-2-pyrazinyl)-4-methylphenyl]-2,2-dimethyl-propanamide수율 45%

실험 절차

The product from Step A (2.0 g, 6.6 mmol) was dissolved in a 30% solution of hydrobromic acid/acetic acid (18.0 mL). This mixture was stirred at room temperature for four days. The mixture was poured into aqueous 1M sodium carbonate (150 mL) and then extracted with ethyl acetate (5×50 mL). The combined extracts were dried (MgSO4) and then evaporated. The solid residue was recrystallized from hexane to afford 1.0 g (45%) of the title compound melting at 74°-76° C. 1H NMR (400 MHz, CDCl3) δ 10.64 (br s, 1H), 8.92 (s, 1H), 8.66 (s, 1H), 8.38 (m, 1H), 729-7.43 (s, 1H), 7.29-7.32 (m, 1H), 2.39 (s, 3H), 1.33 (s, 9H). Mass spec (EI) m/e 349 (1XBr).

후처리

  1. extractionextracted with ethyl acetate (5×50 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customThe solid residue was recrystallized from hexane

출처 및 근거

ORD 기록
ord-c9569bcb07884fe4826d5e30f0fcc607
출처 데이터셋
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05631206

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