Dimethylformamide → 5-(2-Ethoxybenzamido)-1-n-propylimidazole-4-carboxamide

HRID 3645

반응식

HRID 3645 반응식
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O)[CH3:8].CN(C)C=O.[NH2:24][C:25]1[N:29]([CH2:30][CH2:31][CH3:32])[CH:28]=[N:27][C:26]=1[C:33]([NH2:35])=[O:34]>ClCCl.N1C=CC=CC=1>[CH2:7]([O:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH:24][C:25]1[N:29]([CH2:30][CH2:31][CH3:32])[CH:28]=[N:27][C:26]=1[C:33]([NH2:35])=[O:34])=[O:14])[CH3:8]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 672522-Ethoxybenzoic acidHCID 123391055-Amino-1-propyl-1H-imidazole-4-carboxamide

생성물 1

HCID 537133095-(2-Ethoxybenzamido)-1-n-propylimidazole-4-carboxamide수율 77%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

Oxalyl chloride (1.74 g, 0.137 mol) was added dropwise to a stirred solution of 2-ethoxybenzoic acid (1.1 g, 0.00663 mol) and dimethylformamide (0.1 ml) in dichloromethane (20 ml) and the resulting mixture stirred at ambient temperature for 4 hours, then evaporated under vacuum. The residue was azeotroped with dichloromethane (2×20 ml), then added dropwise to a stirred solution of 5-amino-1-n-propylimidazole-4-carboxamide (0.9 g, 0.00536 mol) in pyridine (20 ml) The resulting solution was stirred at ambient temperature for 3 days, then evaporated under vacuum. The residue was dissolved in dichloromethane (50 ml), and the solution washed with 1N hydrochloric acid (30 ml), dried (Na2SO4) and evaporated under vacuum. Chromatography of the crude product on silica gel (15 g) using a methanol in dichloromethane elution gradient (2-6% methanol), followed by crystallisation from ethanol, gave the title compound as a colourless solid (1.3 g, 77%), m.p. 182°-184° C. Found: C,60.85; H,6.40; N,18.06. C16H20N4O3 requires C,60.74; H,6.37; N,17.71%.

후처리

  1. customevaporated under vacuum
  2. customThe residue was azeotroped with dichloromethane (2×20 ml)
  3. stirringwas stirred at ambient temperature for 3 days
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  6. washthe solution washed with 1N hydrochloric acid (30 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum
  9. washa methanol in dichloromethane elution gradient (2-6% methanol)
  10. customfollowed by crystallisation from ethanol

출처 및 근거

ORD 기록
ord-7a5e2995d24f4bac852bdb664f6ad601
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05734053

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