Hydrochloric Acid → HCID 51349052, compound

HRID 385067Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:24]#[CH:25])[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]([C:24]#[CH:25])[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

Conditions

Temperature: 100 °C

Procedure

3-(3-cyano-5-ethynyl-4-methoxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (197 mg) was dissolved in N,N-dimethylformamide (2 mL), and lithium chloride (239 mg) was added to the solution, and then the mixture was stirred at 100° C. for 1 hour. 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 purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), and then crystallized from n-hexane-acetone to obtain the title compound (102 mg) as a pale yellow crystal.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with 1N hydrochloric acid and saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
customcrystallized from n-hexane-acetone

Sources & evidence

ORD record: ord-f525e98563574c4497b580386a204830
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367843B2

Reaction notes

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