Hydrochloric Acid → HCID 68108823, compound

HRID 385147Notes

Reaction equation

HRID 385147 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[C:21]=1[O:22]C)[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2].[Cl-].[Li+].Cl>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([O:24][C:25]([F:28])([F:26])[F:27])[C:21]=1[OH:22])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:17])(=[O:18])[CH2:9]1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68108519HCID 68108519, compound

Product 1

HCID 68108823HCID 68108823, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(3-cyano-4-methoxy-5-trifluoromethoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (300 mg) was dissolved in N,N-dimethylformamide (4 mL), and lithium chloride (309 mg) was added to the solution, and then the mixture was stirred at 100° C. for 1 hour. 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 (184 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-a04327d5a220461bbb60ea378587d47e
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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