Hydrochloric Acid → HCID 68109428, compound

HRID 385123Notes

Reaction equation

HRID 385123 reaction equation
C[O:2][C:3]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:6]([C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11](=[O:19])(=[O:18])[CH2:10]2)=[O:8])=[CH:5][C:4]=1[C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27].[Cl-].[Li+].Cl>CN(C)C=O>[OH:2][C:3]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:6]([C:7]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11](=[O:19])(=[O:18])[CH2:10]2)=[O:8])=[CH:5][C:4]=1[C:26]([N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 68109041HCID 68109041, compound

Product 1

HCID 68109428HCID 68109428, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3-[4-methoxy-3-(pyrrolidine-1-carbonyl)-5-trifluoromethylbenzoyl]-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (715 mg) was dissolved in N,N-dimethylformamide (7 mL), and lithium chloride (649 mg) was added to the solution, and then the mixture was stirred at 120° C. for 2 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 (654 mg) as a colorless amorphous product.

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-40bf37ca9a714e2895203fc875b93a3b
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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