BENZOXAZOLE, 2-CHLORO-5-METHOXY- synthesis
- Product Name:BENZOXAZOLE, 2-CHLORO-5-METHOXY-
- CAS Number:49559-34-4
- Molecular formula:C8H6ClNO2
- Molecular Weight:183.59
49559-83-3
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$37.00/250mg
49559-34-4
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$128.00/100mg
Yield: 30%
Reaction Conditions:
with thionyl chloride in N,N-dimethyl-formamide at 80; for 0.5 h;
Steps:
2-chloro-5-methoxybenzo[d]oxazole 6
To a round bottom flask equipped with a bubbler was added 5-methoxybenzo[d]oxazole-2-thiol (2.7g, 14.92mmol) (5a), thionylchloride (14mL) and DMF (0.3mL). Reaction mixture was then heated to 80oC for thirty minutes. Mixture was then cooled to room temperature and dumped onto ice. Aqueous solution was then extracted with ethyl acetate. Organic layers were combined and washed with brine, dried with sodium sulfate, filtered and concentrated to yield a crude red oil. The red oil was then purified on silica (30%:70% ethyl acetate: hexanes) to yield 2-chloro-5-methoxybenzo[d]oxazole (812 mg, 30%yield) as a beige-white solid. LC/MS m/z: 184.0 (MH+).
References:
Ramurthy, Savithri;Aikawa, Mina;Amiri, Payman;Costales, Abran;Hashash, Ahmad;Jansen, Johanna M.;Lin, Song;Ma, Sylvia;Renhowe, Paul A.;Shafer, Cynthia M.;Subramanian, Sharadha;Sung, Leonard;Verhagen, Joelle [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 11,p. 3286 - 3289] Location in patent:supporting information; experimental part
49559-83-3
79 suppliers
$37.00/250mg
49559-34-4
47 suppliers
$128.00/100mg
20734-76-3
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$10.00/250mg
49559-34-4
47 suppliers
$128.00/100mg
1568-70-3
179 suppliers
$15.00/5g
49559-34-4
47 suppliers
$128.00/100mg