Hydrochloric Acid → 2-Chloro-6-fluoro-5-methoxybenzothiazole

HRID 2368096Notes

Reaction equation

N(OC(C)(C)C)=O.[F:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]2[N:13]=[C:14](N)[S:15][C:11]=2[CH:10]=1.[ClH:21]>C(#N)C.[Cl-].[Na+].O.[Cu](Cl)Cl>[Cl:21][C:14]1[S:15][C:11]2[CH:10]=[C:9]([F:8])[C:18]([O:19][CH3:20])=[CH:17][C:12]=2[N:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of copper(II) chloride (546 mg) and tert-butyl nitrite (0.600 mL) in acetonitrile (10 mL) was stirred at 50° C. for 20 min. To the reaction mixture was added a solution of 6-fluoro-5-methoxy-1,3-benzothiazol-2-amine (670 mg) in acetonitrile (10 mL), and the mixture was further stirred at 50° C. for 30 min. 1M Hydrochloric acid and saturated brine were added to the reaction mixture, and the insoluble material was filtered. The filtrate was extracted with ethyl acetate, the filtered insoluble material was dissolved in THF, and the solution was combined with the organic layer. The mixture was applied to silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure and the obtained solid was washed with ethyl acetate/hexane to give the title compound (350 mg).

Workup

stirringthe mixture was further stirred at 50° C. for 30 min
filtrationthe insoluble material was filtered
extractionThe filtrate was extracted with ethyl acetate
dissolutionthe filtered insoluble material was dissolved in THF
customThe solvent was evaporated under reduced pressure
washthe obtained solid was washed with ethyl acetate/hexane

Sources & evidence

ORD record: ord-c3eca9da52ee4295828810fab096eaa5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

Loading…