Hydrochloric Acid → HCID 51349187, compound

HRID 385081Notes

Reaction equation

HRID 385081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([C:23]([F:26])([F:25])[F: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]([C:23]([F:26])([F:25])[F: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 68109122HCID 68109122, compound

Product 1

HCID 51349187HCID 51349187, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-(3-chloro-4-methoxy-5-trifluoromethylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (74 mg) was dissolved in N,N-dimethylformamide (2 mL), lithium chloride (77 mg) was added to the solution, and then the mixture was stirred at 70° C. for 22 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 diethylether to obtain the title compound (65 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 diethylether

Sources & evidence

ORD record
ord-133226d90d0146538b2d6b5eae59b7d2
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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