Hydrochloric Acid → HCID 68109178, compound

HRID 385093Notes

Reaction equation

HRID 385093 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([I: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>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([I: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 68108772HCID 68108772, compound

Product 1

HCID 68109178HCID 68109178, compoundYield 133.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-(3-chloro-5-iodo-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (922 mg) was dissolved in N,N-dimethylformamide (6 mL), and lithium chloride (421 mg) was added to the solution, and then the mixture was stirred at 120° C. for 2.5 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 to obtain the title compound (1.19 g) as a brown oily substance.

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

Sources & evidence

ORD record
ord-9d86e7a85a89485482588e73961ee682
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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