Hydrochloric Acid → HCID 68108615, compound

HRID 385087Notes

Reaction equation

HRID 385087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:23])[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>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F: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:16])(=[O:17])[CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68108317HCID 68108317, compound

Product 1

HCID 68108615HCID 68108615, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(3,5-difluoro-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (453 mg) was dissolved in N,N-dimethylformamide (4 mL), and lithium chloride (559 mg) was added to the solution, and then the mixture was stirred at 100° C. for 16 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 water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) and then crystallized from diethyl ether to obtain the title compound (270 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 purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-6c868d6b8e0b4d62a9d0cbb3b3e0ab72
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

Loading…