Hydrochloric Acid → HCID 68108594, compound

HRID 385136Notes

Reaction equation

HRID 385136 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][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]=[CH:20][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 68109023HCID 68109023, compound

Product 1

HCID 68108594HCID 68108594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

3-(3-cyano-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (2.30 g) was dissolved in N,N-dimethylformamide (25 mL), and lithium chloride (2.97 g) was added to the solution, and then the mixture was stirred at 130° C. for 12 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 used for the synthesis of (g).

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 used for the synthesis of (g)

Sources & evidence

ORD record
ord-f8babcdc82fc4c4d9f595165bd0316fd
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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