Hydrochloric Acid → HCID 54552857, compound

HRID 1649405Notes

Reaction equation

HRID 1649405 reaction equation
C([O:3][C:4](=[O:19])[C:5]([C:13]1[N:14]=[C:15]([NH2:18])[S:16][CH:17]=1)=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.Cl>O1CCOCC1.[OH-].[Na+]>[NH2:18][C:15]1[S:16][CH:17]=[C:13]([C:5](=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([OH:19])=[O:3])[N:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54434053HCID 54434053, compound

Product 1

HCID 54552857HCID 54552857, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

216 g of the crude product from Example 30 were dissolved in a mixture of 1.2 liters of dioxane and 800 ml of 12 percent strength sodium hydroxide solution. The solution was boiled under reflux for 15 hours and the dioxane was then stripped off and the residue was adjusted to pH 8 with 2 N hydrochloric acid. The mixture was extracted three times with ethyl acetate, the aqueous solution was adjusted to pH 3 to 4 and the product which had precipitated was filtered off. 20 g of the desired product of melting point 138° could be obtained directly by recrystallization from methanol. The mother liquor consisted of an E/Z mixture, which could not be separated by crystallization.

Workup

  1. temperatureunder reflux for 15 hours
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. customthe product which had precipitated
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-9ba8484a38b94fd49486f55313e5f38b
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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