Benzaldehyde → Methyl 1-[4-(N-benzylamino)-benzyl]-2-butyl-4-chloroimidazole-5-acetate

HRID 466391노트

반응식

HRID 466391 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:10]([Cl:17])[N:9]=[C:8]2[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[CH2:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:10]([Cl:17])[N:9]=[C:8]2[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:22][CH:23]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

4

반응물 2

HCID 240Benzaldehyde2회HCID 15356445Methyl 1-(4-aminobenzyl)-2-butyl-4-chloroimidazole-5-acetate

생성물 1

HCID 19815423Methyl 1-[4-(N-benzylamino)-benzyl]-2-butyl-4-chloroimidazole-5-acetate수율 57.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of methyl 1-(4-aminobenzyl)-2-butyl-4-chloroimidazole-5-acetate (1.00 g, 3.0 mmol, 1 eq), benzaldehyde (0.30 mL, 3.0 mmol, 1 eq), 4A° powdered molecular sieves (enough to make a slurry) and 40 mL THF was stirred overnight. The next day, more benzaldehyde (0.2 mL) and acidic Al2O3 (activity 1, 1 g) were added and the slurry stirred another 24 hours. The solids were filtered and the solvent from the filtrate removed in vacuo. The residue was dissolved in methanol (10 mL) and sodium cyanoborohydride was added (0.19 g, 3.0 mmol, 1 eq). The mixture was stirred for 24 hours, after which the solvent was removed in vacuo to yield a green oil which was flash chromatographed over silica gel in 70:30 hexane/ethyl acetate to give 740 mg of product as an oil. NMR (200 MHz, CDCl3) δ 7.42-7.24 (m, 5H); 6.74 (d, 2H, J=7 Hz); 6.56 (d, 2H, J=7 Hz); 4.98 (s, 2H); 4.31 (s, 2H); 3.61 (s, 3H); 3.48 (s, 2H); 2.60 (t, 2H, J=7 Hz); 1.67 (t of t, 2H, J=7,7 Hz); 1.35 (t of q, 2H, J=7,7 Hz); 0.89 (t, 3H, J=7 Hz). Mass Calcd. for C24H28ClN3O2 : 425.1868. Found: 425.1853.

후처리

  1. stirringthe slurry stirred another 24 hours
  2. filtrationThe solids were filtered
  3. customthe solvent from the filtrate removed in vacuo
  4. dissolutionThe residue was dissolved in methanol (10 mL)
  5. additionsodium cyanoborohydride was added (0.19 g, 3.0 mmol, 1 eq)
  6. stirringThe mixture was stirred for 24 hours
  7. customafter which the solvent was removed in vacuo
  8. customto yield a green oil which
  9. customchromatographed over silica gel in 70:30 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-35187dc5b911417ca015e0ee6f640285
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155118

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