Hydrochloric Acid → HCID 68108172, compound

HRID 385162Notes

Reaction equation

HRID 385162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:27])[C:24]=1[O:25]C)[C:5]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:10]=2[S:9](=[O:21])(=[O:20])[CH2:8]1)=[O:6].[Cl-].[Li+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:27])[C:24]=1[OH:25])[C:5]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]([F:18])([F:19])[F:17])[CH:14]=[CH:15][C:10]=2[S:9](=[O:20])(=[O:21])[CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68108576HCID 68108576, compound

Product 1

HCID 68108172HCID 68108172, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-(3,5-dichloro-4-methoxybenzoyl)-1,1-dioxo-5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole (209 mg) was dissolved in N,N-dimethylformamide (2 mL), lithium chloride (106 mg) was added to the solution, and then the mixture was stirred at 120° C. for 2 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-chloroform to obtain the title compound (167 mg) as a pale yellow 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-chloroform

Sources & evidence

ORD record
ord-09d41f1ee92d4711ab2ac15890e07385
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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