Ethanol → HCID 67823296, compound

HRID 1492568Notes

Reaction equation

HRID 1492568 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH:17]([C:25]2[CH:36]=[CH:35][C:28]([CH:29]=[C:30]([CH3:34])[C:31]([OH:33])=[O:32])=[CH:27][CH:26]=2)[CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[CH2:37](O)[CH3:38].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH2:16][CH:17]([C:25]2[CH:26]=[CH:27][C:28]([CH:29]=[C:30]([CH3:34])[C:31]([O:33][CH2:37][CH3:38])=[O:32])=[CH:35][CH:36]=2)[CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 86748335HCID 86748335, compound

Product 1

HCID 67823296HCID 67823296, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 0.60 g of 4-[1-(4-chlorobenzenesulfonamido)-3-(3-pyridyl)-2-propyl]-α-methylcinnamic acid thionyl chloride and stirred for one hour. To the mixture was added 5 ml of ethanol at 0° C., and stirred for three hours, followed by dropwise addition of saturated aqueous sodium hydrogencarbonate and extraction with ethyl acetate and then further washing in saturated aqueous sodium chloride solution, and dried over magnesium sulfate to distill off the solvent. The residue obtained was subjected to chromatography on a silica gel column, and from a fraction eluted with methanol-methylene chloride (5:95 v/v) was obtained 0.49 g of ethyl 4-[1-(4-chlorobenzenesulfonamido)-3-(3-pyridyl)-2-propyl]-α-methylcinnamate.

Workup

  1. washfurther washing in saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. distillationto distill off the solvent
  4. customThe residue obtained
  5. washfrom a fraction eluted with methanol-methylene chloride (5:95 v/v)

Sources & evidence

ORD record
ord-a07d1d3168814765a974ef1bf95bcaf9
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

Loading…