Imidazole → Methyl 8-(p-chlorophenylsulfonamido)-4-[2-(1-imidazolyl)ethyl]-octanoate

HRID 465549Notes

Reaction equation

HRID 465549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24]OS(C)(=O)=O)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 10050375Methyl 8-(p-chlorophenylsulfonamido)-4-(2-methylsulfonyloxyethyl)-octanoate

Product 1

HCID 10094868Methyl 8-(p-chlorophenylsulfonamido)-4-[2-(1-imidazolyl)ethyl]-octanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.218 g methyl 8-(p-chlorophenylsulfonamido)-4-(2-methylsulfonyloxyethyl)-octanoate in 2 ml dimethylformamide is added 0.101 g imidazole and then the solution is heated at 100° for 8 h. The mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with water (2×20 ml), dried, filtered and evaporated to give an amber oil which is purified by preparative thin layer chromatography using ethyl acetate as eluent to give methyl 8-(p-chlorophenylsulfonamido)-4-[2-(1-imidazolyl)ethyl]-octanoate as a yellow oil.

Workup

  1. temperaturethe solution is heated at 100° for 8 h
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water (2×20 ml)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give an amber oil which
  8. customis purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-2cf41ce4ff1a43cb855f34ef30eea0aa
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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