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Dimethyl Sulfoxide → 1,3-dihydro-1-[2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]-2-oxoethyl]-2H-imidazol-2-one

HRID 431071
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HRID 431071 반응식
[Cl-].[Cl-].C(O)(O)C.CS(C)=O.[OH:11][CH:12]([C:20]1[CH:25]=[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:23]([O:38][CH3:39])=[CH:22][N:21]=1)[CH2:13][N:14]1[CH:18]=[CH:17][NH:16][C:15]1=[O:19].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:39][O:38][C:23]1[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:25][C:20]([C:12](=[O:11])[CH2:13][N:14]2[CH:18]=[CH:17][NH:16][C:15]2=[O:19])=[N:21][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 98870641,3-dihydro-1-[2-hydroxy-2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]ethyl]-2H-imidazol-2-one2회HCID 18763373Ethanediol dichloride

생성물 1

HCID 187633691,3-dihydro-1-[2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]-2-oxoethyl]-2H-imidazol-2-one수율 69.6%

시약·촉매·용매

2
HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

Reaction under N2. A solution of ethanediol dichloride (0.0210 mol) in CH2Cl2 (40 ml) was stirred at −60° C. A solution of dimethyl sulfoxide (0.0420 mol) in CH2Cl2 (10 ml) was added dropwise and stirring was continued for 5 min at −60° C. A solution of 1,3-dihydro-1-[2-hydroxy-2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]ethyl]-2H-imidazol-2-one (compound 18) (0.0070 mol) in CH2Cl2 (10 ml) was added dropwise at −60° C. and stirring was continued for 15 min at −60° C. Triethylamine (0.0770 mol) was added dropwise at −60° C. and stirring was continued for 5 min. The mixture was treated with water, then extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 94/6). The pure fractions were collected and the solvent was evaporated, yielding 1.8 g (69.6%) of 1,3-dihydro-1-[2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]-2-oxoethyl]-2H-imidazol-2-one (interm. 11).

후처리

  1. customReaction under N2
  2. stirringstirring
  3. waitwas continued for 15 min at −60° C
  4. stirringstirring
  5. waitwas continued for 5 min
  6. extractionextracted with CH2Cl2
  7. dry with materialThe separated organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 94/6)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-00d89fbf58e740a29606270e420d5782
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06656959B1

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