Hydrochloric Acid → HCID 51349185, compound

HRID 385063Notes

Reaction equation

HRID 385063 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([CH:24]2[CH2:26][CH2:25]2)[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]([CH:24]2[CH2:26][CH2:25]2)[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 68108745HCID 68108745, compound

Product 1

HCID 51349185HCID 51349185, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(3-cyano-5-cyclopropyl-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (142 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (163 mg) was added to the solution, and then the mixture was stirred at 100° C. for 23 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 (115 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-225525a6dc1b4d51bc894396f3af694a
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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