Hydrochloric Acid → HCID 13543995, compound

HRID 904687Notes

Reaction equation

HRID 904687 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[CH:7]2)(=[O:3])[CH3:2].[C:22](OCC)(=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].[O-][CH2:33]C.[Na+].[Na].Cl>C(O)C.C(OCC)(=O)C>[O:3]=[C:1]1[C:4]2[CH:5]=[C:6]3[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=2[O:14][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:2]1)[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:33])=[O:19])[CH:8]=[CH:7]3

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 135773203HCID 135773203, compound

Product 1

HCID 13543995HCID 13543995, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The product of step (a) (1.75 g), and diethyl oxalate (4.38 g) dissolved in dry ethanol (50 mls) was added to sodium ethoxide solution (prepared by the addition of sodium (0.35 g), to dry ethanol (50 mls) with stirring. The reaction mixture was stirred under reflux for 1 hr, cooled, poured into ethyl acetate and dilute hydrochloric acid and the organic layer separated, washed well with water and dried. The solvent was evaporated and the residue treated with ethanol saturated with hydrogen chloride gas (100 mls) and refluxed for 10 mins. The reaction mixture was cooled, poured into water, and the precipitated product collected by filtration, washed well with water and dried to give 2.5 g of product. A recrystallisation from ethanol gave 1.25 g, mp 168°-171°.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 1 hr
  3. temperaturecooled
  4. customthe organic layer separated
  5. washwashed well with water
  6. customdried
  7. customThe solvent was evaporated
  8. additionthe residue treated with ethanol saturated with hydrogen chloride gas (100 mls)
  9. temperaturerefluxed for 10 mins
  10. temperatureThe reaction mixture was cooled
  11. additionpoured into water
  12. filtrationthe precipitated product collected by filtration
  13. washwashed well with water
  14. customdried

Sources & evidence

ORD record
ord-fd45cdceebfe437e9b3ee80e073600a8
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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