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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
Notes
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Reaction equation

HRID 431071 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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×HCID 18763373Ethanediol dichloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-00d89fbf58e740a29606270e420d5782
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06656959B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes