Hydrochloric Acid → HCID 23333818, compound

HRID 904230Notes

Reaction equation

HRID 904230 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:23])[O:22][C:14]2(C(OC)=O)[C:15]([NH2:17])=[O:16])=[CH:9][CH:8]=1.[OH-].[K+].Cl>CO>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:23])[C:14](=[O:22])[C:15]([NH2:17])=[O:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23333832HCID 23333832, compound

Product 1

HCID 23333818HCID 23333818, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 5 ml of methanol was dissolved 3.32 g (0.010 mole) of 3-[4-(3-methyl-2-thienyl)phenyl]-2,3-epoxy-2-methoxycarbonylbutyramide, followed by gradual addition of 15 ml (0.015 mole) of 1 N methanol solution of potassium hydroxide. The mixture was stirred at room temperature for one hour and freed from methanol by distillation under reduced pressure, and 40 ml of water was added thereto and 20 ml of benzene was then added to remove impurities, and the mixture was shaken thoroughly. The aqueous layer was separated, and 17 ml (0.017 mole) of 1 N hydrochloric acid was gradually added thereto, after which the mixture was heated with stirring to 90° C. to effect decarboxylation. After one hour of heating, the aqueous mixture was cooled and extracted with 70 ml of diethyl ether. The ether extract solution was dried over anhydrous magnesium sulfate and freed from diethyl ether by distillation under reduced pressure to obtain 2.10 g (77% yield) of 3 -[4-(3-methyl-2-thienyl)phenyl]-2-oxobutyramide.

Workup

  1. distillationfreed from methanol by distillation under reduced pressure, and 40 ml of water
  2. additionwas added
  3. addition20 ml of benzene was then added
  4. customto remove impurities
  5. stirringthe mixture was shaken thoroughly
  6. customThe aqueous layer was separated
  7. temperatureafter which the mixture was heated
  8. stirringwith stirring to 90° C.
  9. temperatureAfter one hour of heating
  10. temperaturethe aqueous mixture was cooled
  11. extractionextracted with 70 ml of diethyl ether
  12. extractionThe ether extract solution
  13. dry with materialwas dried over anhydrous magnesium sulfate
  14. distillationfreed from diethyl ether by distillation under reduced pressure

Sources & evidence

ORD record
ord-4f8b73304dd048289eae8f52c7288ee7
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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