Hydrochloric Acid → HCID 66939200, compound

HRID 1257374Notes

Reaction equation

HRID 1257374 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[S:9][C:10]=1[Br:11])(=O)C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[Br:11][C:10]1[S:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[CH:13]=2)=[N:7][C:6]=1[CH2:5][OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66938946HCID 66938946, compound

Product 1

HCID 66939200HCID 66939200, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixed solution of the compound (2.0 g, 5.3 mmol) obtained in Example 64d in ethanol/tetrahydrofuran (v/v=1/1, 20 mL) was added 2N aqueous sodium hydroxide solution (5.3 mL, 11 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (1.6 g, 89%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-4abc179eba8d41c184f557b468948f92
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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