Hydrochloric Acid → HCID 51349181, compound

HRID 385036Notes

Reaction equation

HRID 385036 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:26]#[N:27])[C:23]=1[O:24]C)[C:8]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:20])(=[O:19])[CH2:11]1)=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].Cl>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:26]#[N:27])[C:23]=1[OH:24])[C:8]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12](=[O:19])(=[O:20])[CH2:11]1)=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68108747HCID 68108747, compound

Product 1

HCID 51349181HCID 51349181, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-(3-t-butyl-5-cyano-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (364 mg) was dissolved in N,N-dimethylformamide (4 mL), and lithium chloride (401 mg) was added to the solution, and then the mixture was stirred at 120° C. for 16 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-ethyl acetate to obtain the title compound (299 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-e5b9a7da126d46f3813cd9200d60d8c6
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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