Hydrochloric Acid → HCID 68109051, compound

HRID 385130Notes

Reaction equation

HRID 385130 reaction equation
[OH:1][C:2]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:5]([C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10](=[O:18])(=[O:17])[CH2:9]2)=[O:7])=[CH:4][C:3]=1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26].[OH:32]OS([O-])=O.[K+].Cl>O1CCCC1.O>[OH:1][C:2]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:5]([C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10](=[O:18])(=[O:17])[CH2:9]2)=[O:7])=[CH:4][C:3]=1[C:25]([N:27]1[CH2:31][CH2:30][S:29](=[O:32])[CH2:28]1)=[O:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23707502Potassium hydroxy sulfiteHCID 68109415HCID 68109415, compound

Product 1

HCID 68109051HCID 68109051, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[4-hydroxy-3-(1,3-thiazolidine-3-carbonyl)-5-trifluoromethylbenzoyl]-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (67 mg) was dissolved in tetrahydrofuran (0.5 mL) and water (0.5 mL), and oxone (45 mg) was added to the solution, and then the mixture was stirred at room temperature for 1 hour. To the reaction solution, 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was crystallized from n-hexane-chloroform to obtain the title compound (46 mg) as a colorless crystal.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was crystallized from n-hexane-chloroform

Sources & evidence

ORD record
ord-58f94baaf9a84051b20403633ce7d84c
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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