Hydrochloric Acid → HCID 68109164, compound

HRID 385157Notes

Reaction equation

HRID 385157 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[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]([O:23][C:24]([F:27])([F:26])[F:25])[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 68108108HCID 68108108, compound

Product 1

HCID 68109164HCID 68109164, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-(3-chloro-4-methoxy-5-trifluoromethoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (420 mg) was dissolved in N,N-dimethylformamide (5 mL), and lithium chloride (421 mg) was added to the solution, and then the mixture was stirred at 120° C. for 14 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-ethyl acetate to obtain the title compound (182 mg) as a colorless 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-ethyl acetate

Sources & evidence

ORD record
ord-f1e59921f18a4afe8d49f9053c773155
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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