Hydrochloric Acid → HCID 68108354, compound

HRID 385097Notes

Reaction equation

HRID 385097 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([S:22][CH3:23])[C:20]=1[OH:21])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:17])(=[O:16])[CH2:8]1)=[O:6].[OH:24]OS([O-])=O.[K+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([S:22]([CH3:23])=[O:24])[C:20]=1[OH:21])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:17])(=[O:16])[CH2:8]1)=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23707502Potassium hydroxy sulfiteHCID 51349323HCID 51349323, compound

Product 1

HCID 68108354HCID 68108354, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(3-chloro-4-hydroxy-5-methylsulfanylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (51 mg) was dissolved in tetrahydrofuran (0.5 mL) and water (0.5 mL), and oxone (43 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-diethylether to obtain the title compound (45 mg) as a brown 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-diethylether

Sources & evidence

ORD record
ord-96c6aed9b27f442fbb3e0f00d607995a
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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