Hydrochloric Acid → HCID 51349057, compound

HRID 385027Notes

Reaction equation

HRID 385027 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([C:23]#[N: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]#[N: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:16])(=[O:17])[CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68109124HCID 68109124, compound

Product 1

HCID 51349057HCID 51349057, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(3-chloro-5-cyano-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (180 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (87 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 reaction 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 (146 mg) as a pale yellow crystal.

Workup

  1. customreaction mixture
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was crystallized from n-hexane-chloroform

Sources & evidence

ORD record
ord-5f9ffddc80ed4599a6349a45531f8f15
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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