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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
ノート
印刷プレビュー

反応式

HRID 431071 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 98870641,3-dihydro-1-[2-hydroxy-2-[5-methoxy-4-[(5-phenylpentyl)oxy]-2-pyridinyl]ethyl]-2H-imidazol-2-one2 回HCID 18763373Ethanediol dichloride

生成物 1

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

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-00d89fbf58e740a29606270e420d5782
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06656959B1

反応ノート

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