Hydrochloric Acid → HCID 51349323, compound

HRID 385095Notes

Reaction equation

HRID 385095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([S:23][CH3:24])[C:20]=1[O:21]C)[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].[Cl-].[Li+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([S:23][CH3:24])[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68108455HCID 68108455, compound

Product 1

HCID 51349323HCID 51349323, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-(3-chloro-4-methoxy-5-methylsulfanylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (203 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (258 mg) was added to the solution, and then the mixture was stirred at 120° C. for 20 hours. To the reaction solution, 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid 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 (169 mg) as a brown crystal.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid 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-4376643e5026434fadf8eecf7b0b8bfd
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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