Chloroform → 6-{3-[N-(2-benzoyloxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril

HRID 1903196Notes

Reaction equation

HRID 1903196 reaction equation
C(Cl)(Cl)Cl.[OH:5][CH2:6][CH2:7][N:8]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:9]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH:19]=[CH:18]2)=[O:10].C(N(CC)CC)C.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)(Cl)Cl.CO>[C:39]([O:5][CH2:6][CH2:7][N:8]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:9]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH:19]=[CH:18]2)=[O:10])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 12866343N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

Product 1

HCID 131079636-{3-[N-(2-benzoyloxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Into 100 ml of chloroform were added 3.7 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril and 1.8 ml of triethylamine and the outside of the reaction vessel containing said mixture was ice-cooled. Then 1.4 ml of benzoyl chloride was added dropwise to the mixture under stirring condition. After the addition operation the reaction mixture was further stirred at room temperature for 1 hour. Then the reaction mixture was washed with 5% NaHCO3 aqueous solution, diluted hydrochloric acid and water in this order, then dried with anhydrous sodium sulfate. The drying agent was removed by filtration and the mother liquor is concentrated. The residue thus obtained is treated by a silica-gel column chromatography [the solvent used was a mixture of chloroform:methanol 30:1 (v/v)] and the elute was recrystallized from chloroform-petroleum ether to obtain 3.0 g of 6-{3-[N-(2-benzoyloxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril as in the form of colorless needle-like crystals. Melting point: 94°-96° C.

Workup

  1. additionthe outside of the reaction vessel containing
  2. temperaturecooled
  3. stirringAfter the addition operation the reaction mixture was further stirred at room temperature for 1 hour
  4. washThen the reaction mixture was washed with 5% NaHCO3 aqueous solution, diluted hydrochloric acid and water in this order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe mother liquor is concentrated
  8. customThe residue thus obtained
  9. additionis treated by a silica-gel column chromatography [the solvent
  10. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-455d907b1d194378b85b51a7787f5a4a
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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