Hydrochloric Acid → HCID 51349186, compound

HRID 385077Notes

Reaction equation

HRID 385077 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([S:24][CH3:25])[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]([S:24][CH3:25])[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:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68109280HCID 68109280, compound

Product 1

HCID 51349186HCID 51349186, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(3-cyano-4-methoxy-5-methylsulfanylbenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (142 mg) was dissolved in N,N-dimethylformamide (1 mL), and lithium chloride (64 mg) was added to the solution, and then the mixture was stirred at 100° C. for 1.5 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 (95 mg) as a 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-ac5da7251c034c7da37cc0f79888397a
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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