Sulfuric Acid → methyl N-(3,4-dibromobenzoyl)-6-aminohexanoate

HRID 987171노트

반응식

HRID 987171 반응식
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=1[Br:24])[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:11].[C:25]([O-])(O)=O.[Na+]>CO>[Br:6][C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=1[Br:24])[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:25])=[O:19])=[O:11]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22988601N-(3,4-dibromobenzoyl)-6-aminohexanoic acid

생성물 1

HCID 22988604methyl N-(3,4-dibromobenzoyl)-6-aminohexanoate수율 96%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Added conc. H2SO4 (0.2 mL) to a solution of N-(3,4-dibromobenzoyl)-6-aminohexanoic acid (1.73 g, 4.4 mmol) in methanol (50 mL). Heated under reflux for 2 hours until reaction complete (as determined by TLC). Allowed solution to cool to room temperature and neutralized by adding NaHCO3 solution. Removed solvent in vacuo and extracted residue with ether (2×50 mL). Washed extract with brine (2×30 mL) and dried over anhydrous MgSO4. Filtered extract and dried filtrate under high vacuum to afford a white solid. Obtained 1.72 g (96% yield) of methyl N-(3,4-dibromobenzoyl)-6-aminohexanoate. 1H NMR (300 MHz, DMSO-d6): δ8.59 (triplet, J=5.7 Hz, 1H), 8.16 (doublet, J=1.8 Hz, 1H), 7.84 (doublet, J=8.1 Hz, 1H), 7.73 (doublet of doublets, J=8.1, 1.8 Hz, 1H), 3.55 (singlet, 3H), 3.21 (doublet of triplets, J=6.0, 6.6 Hz, 2H), 2.28 (triplet J=7.3 Hz, 2H), 1.51 (multiplet, 4H), 1.28 (multiplet, 2H). 13C NMR (300 MHz, DMSO-d6): δ173.55, 164.05, 135.67, 133.96, 132.31, 128.20, 127.09, 124.13, 51.19, 39.20, 33.21, 28.56, 25.89, 24.15.

후처리

  1. temperatureHeated
  2. temperatureunder reflux for 2 hours until reaction complete (as determined by TLC)
  3. extractionRemoved solvent in vacuo and extracted residue with ether (2×50 mL)
  4. washWashed
  5. extractionextract with brine (2×30 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationFiltered
  8. extractionextract
  9. customdried filtrate under high vacuum to afford a white solid

출처 및 근거

ORD 기록
ord-1c17ce149584488da34e311784c996eb
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630577B2

반응 노트

불러오는 중…