Hydrochloric Acid → HCID 70109854, compound

HRID 1421992Notes

Reaction equation

HRID 1421992 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH:24]=[CH:25][C:26]([O:28]CC)=[O:27])[C:21]([O:31]COC)=[C:20]([C:35]([O:37]COC)=[O:36])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].Cl.[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])[C:21]([OH:31])=[C:20]([C:35]([OH:37])=[O:36])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53646561HCID 53646561, compound

Product 1

HCID 70109854HCID 70109854, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

In 10 ml of ethanol was dissolved 350 mg of 2-(3,4-diethoxyphenyl)-4-[3-methoxymethoxycarbonyl-4-methoxymethoxy-5-(2-ethoxycarbonylvinyl)phenyl]thiazole. Thereto was added 0.2 ml of 10% hydrochloric acid. The mixture was stirred at 60° C. for 1 hour with heating. Thereto was added 1 ml of 10% sodium hydroxide. The mixture was refluxed for 4 hours with heating. The solvent was removed from the reaction mixture by distillation. The residue was mixed with 15 ml of water. The mixture was made weakly acidic with 10% hydrochloric acid and extracted with 40 ml of hot ethyl acetate. The organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution, dried and subject to distillation to remove the solvent. The residue was recrystallized from ethyl acetate to obtain 170 mg of 2-(3,4-diethoxyphenyl)-4-[3-carboxy-4-hydroxy-5-(2-carboxyvinyl)phenyl]thiazole.

Workup

  1. temperaturewith heating
  2. temperatureThe mixture was refluxed for 4 hours
  3. temperaturewith heating
  4. customThe solvent was removed from the reaction mixture by distillation
  5. additionThe residue was mixed with 15 ml of water
  6. extractionextracted with 40 ml of hot ethyl acetate
  7. washThe organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution
  8. customdried
  9. distillationsubject to distillation
  10. customto remove the solvent
  11. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1fb46e197d414fc59a37cd7259f55032
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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