Hydrochloric Acid → HCID 71224338, compound

HRID 2402940Notes

Reaction equation

HRID 2402940 reaction equation
C([O:3][C:4]([C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]=[C:8]([S:17][CH3:18])[N:7]=1)=[CH2:5])C.Cl>C(O)C>[C:4]([C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]=[C:8]([S:17][CH3:18])[N:7]=1)(=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86676021HCID 86676021, compound

Product 1

HCID 71224338HCID 71224338, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 1A (2.0 g, 7.45 mmol) in a solvent mixture of ethanol (24.84 ml) and 10% HCl solution (4.53 ml, 14.91 mmol) was heated to 50° C. for 18 hours. The reaction mixture was cooled, and the majority of the ethanol removed by rotary evaporation. The residue was partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate. The combined organics were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound, which was used in the subsequent step without further purification. MS ESI(+) m/z 241 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe majority of the ethanol removed by rotary evaporation
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with additional ethyl acetate
  6. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad23b9de4e9e46b6b74154090ce9fda0
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

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