Sodium ethoxide → HCID 15572903, compound

HRID 1154947Notes

Reaction equation

HRID 1154947 reaction equation
C(O[C:4]([CH2:6][CH:7]([CH3:21])[CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]2)=[O:5])C.CC[O-].[Na+].[CH3:26][NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[CH3:34]>C(O)C>[CH3:26][N:27]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[CH3:34])[C:4]([CH2:6][CH:7]([CH3:21])[CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]2)=[O:5]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 15921594HCID 15921594, compoundHCID 20563580HCID 20563580, compound

Product 1

HCID 15572903HCID 15572903, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.7 Grams of 6-(3-ethoxycarbonyl-2-methylpropoxy)carbostyril, 0.5 g of sodium ethylate and 5 ml of N-methyl-2-methylcyclohexylamine are added to 100 ml of ethanol, and the mixture is reacted in an autoclave under 110 atm. and at 140° to 150° C. for 6 hours. After cooling, the reaction solution is concentrated under reduced pressure and the residue is dissolved in 200 ml of chloroform, washed with a 1% aqueous K2CO3 solution, diluted hydrochloric acid and water in that order and then dried with anhydrous Na2SO4. The solvent is distilled off and the residue is refined by silica gel column chromatography (silica gel: Wakogel C-200; eluent: 20/1 (V/V) chloroform-methanol) and the obtained crude crystals are recrystallized from benzene-ligroin, resultantly obtaining 1.0 g of 6-{3-[N-methyl-N-(2-methylcyclohexyl)aminocarbonyl]-2-methylpropoxy}carbostyril in the form of colorless needle-like crystals with melting point of 146°-149° C.

Workup

  1. customthe mixture is reacted in an autoclave under 110 atm. and at 140° to 150° C. for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction solution is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in 200 ml of chloroform
  5. washwashed with a 1% aqueous K2CO3 solution, diluted hydrochloric acid and water in that order
  6. dry with materialdried with anhydrous Na2SO4
  7. distillationThe solvent is distilled off
  8. customthe obtained crude crystals
  9. customare recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-02a52b6b5bd14d88bcfd33d22429056a
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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