Ethylene Glycol → 6-(1-Ethylenedioxy-4-chlorobutyl)-3,4-dihydrocarbostyril

HRID 1085111Notes

Reaction equation

HRID 1085111 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)=[O:6].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na]>C1C=CC=CC=1>[CH2:18]1[CH2:19][O:20][CH:4]([CH2:3][CH2:2][Cl:1])[CH:5]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[O:6]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 5360545SodiumHCID 128335166-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

Product 1

HCID 1317168246-(1-Ethylenedioxy-4-chlorobutyl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 Grams (39.7 mM) of 6-(4-chlorobutyryl)-3,4-dihydrocarbostyril was dissolved in 300 ml of benzene, then to this solution was added 7.4 g (120 mM) of ethylene glycol and 300 mg of p-toluenesulfonic acid, and the whole mixture was refluxed by heating under dehydrating in Dean-Stark extractor for 6 hours. The reaction mixture was cooled and neutralized with an aqueous solution saturated with sodium hyfrogen carbonate, then extracted with chloroform. The chloroform extract was washed with water then dried with anhydrous magnesium sulfate, then concentrated by removing the solvent by evaporation. The residue thus obtained was purified by means of a silicagel column chromatography (eluent: chloroform:methanol=40:1) to yield 10.5 g of 6-(1-ethylenedioxy-4-chlorobutyl)-3,4-dihydrocarbostyril.

Workup

  1. temperaturethe whole mixture was refluxed
  2. temperatureby heating under dehydrating in Dean-Stark extractor for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with water
  7. dry with materialthen dried with anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customby removing the solvent
  10. customby evaporation
  11. customThe residue thus obtained
  12. customwas purified by means of a silicagel column chromatography (eluent: chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-91bed590b18443869671f054e4cea870
Source dataset
uspto-grants-1991_04
Patent number
US05008274

Reaction notes

Loading…