5-Chloro-2-methylbenzoxazole

BEIGE CRYSTALLINE CHUNKS

General procedure: To a stirred solution of ortho-hydroxyaryl N–H ketimines 1 (1mmol) in solvent (2mL) was added an additive if specified (0.2–1.0mmol) and PhI(OAc)Step (1), 5-chloro-o-hydroxy acetophenone imine as raw material, Iodobenzene diacetate as oxidant, triethylamine as additive, In methanol solvent, according to 5-chloro o-hydroxy acetophenone imine millimoles:Iodobenzene diacetate millimoles: triethylamine millimoles: methanol methanol ratio of 1: 1 5: 0: 2 ratio, the reactor was added 5-chloro-o-hydroxy acetophenone imine (169.6mg) And methanol (2 mL) were added, and finally iodobenzene diacetate (483.2 mg, 1.5 mmol) was added with stirring. After completion of the addition, stirring and oxidation were carried out continuously for 30 minutes at room temperature to prepare a benzoxazole derivative The reaction solution. Step (2), the eluent is a mixture of ethyl acetate: petroleum ether in a ratio of 1:40 to give a white solid 5-chloro-2-Methylbenzoxazole (125.7 mg, 75percent yield).General procedure: To a mixture of orthoester (1.1 mmol) and o-aminophenol or o-aminothiophenol (1 mmol) was added TSA (1 molpercent). The mixture was stirred at 80–90 °C for the appropriate time according to Table 4. After the completion of the reaction (as indicated by TLC), the mixture was diluted with chloroform (10 mL) and the catalyst was separated by filtration. Further purification was achieved by column chromatographyGeneral procedure: A mixture of 2-amino(thio)phenols (1, 1.5 mmol) and b-oxodi-thioesters (2, 1.0 mmol) were placed in 10 mL round bottom ask. p-Toluenesulfonic acid monohydrate (PTSA) (10 mol percent) and 1 mL ofacetonitrile was added to make homogenous paste. The mixturewas stirred at 90 C for stipulated period of time (in open atmo-sphere). After the completion of the reaction (monitored by TLC), the reaction mixture was quenched with H2O and extracted withEtOAc. The organic layer was separated, washed with water twice, dried over anhydrous Na2SO4, and concentrated under reducedpressure. The crude reaction mixture was puried by columnchromatography on silica gel (100e200 mesh) using ethyl acetate/hexanes as the eluting system. The identity and purity of productwas conrmed by 1H, 13C, 19F NMR spectroscopic and MS/HRMSanalysis.General procedure: To a mixture of o-substituted (–NH2 or –SH or –OH) anilines(1.0 mmol) and appropriate 1, 3-diketones (1.1 mmol) in THF(5 mL) was added 30percentw/w aqueous NaICl2 (0.2 mmol, 20molpercent). The reaction was allowed to remain stirred at refluxtemperature for 2–3 h. After the reaction was complete, asindicated by TLC, the mixture was cooled to room temperature.The volatiles were removed under reduced pressureand treated successively with aqueous sodium thiosulphatesolution and saturated solution of NaHCO3, and extractedby ethylacetate (2×10 mL). The combined organic phaseswere washed with brine and dried over Na2SO4 and evaporatedunder vacuum. The crude reaction mixture was purifiedby column chromatography on silica gel using petroleumether/ethyl acetate as eluents.

Molecular Weight:167.59
XLogP3:2.8
Hydrogen Bond Acceptor Count:2
Exact Mass:167.0137915
Monoisotopic Mass:167.0137915
Topological Polar Surface Area:26
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes