Hydrochloric Acid → HCID 68108353, compound

HRID 385028Notes

Reaction equation

HRID 385028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:21]#[N:22])[C:18]=1[O:19]C)[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8]1)=[O:6].[Cl-].[Li+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:21]#[N:22])[C:18]=1[OH:19])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 681080913-(3-Chloro-5-cyano-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole

Product 1

HCID 68108353HCID 68108353, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-chloro-5-cyano-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole (213 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (111 mg) was added to the solution, and then the mixture was stiffed at 100° C. for 2 hours. To the reaction solution, 1N hydrochloric acid was added, and then the 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 purified by silica gel column chromatography (ethyl acetate:methanol=10:1), and then crystallized from n-hexane-chloroform to obtain the title compound (68 mg) as a pale yellow crystal.

Workup

  1. extractionthe reaction 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 purified by silica gel column chromatography (ethyl acetate:methanol=10:1)
  6. customcrystallized from n-hexane-chloroform

Sources & evidence

ORD record
ord-0e563d028bec44f8ba754077fcaa184e
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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