5-[(4-chlorophenoxy)methyl]-3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazole synthesis
- Product Name:5-[(4-chlorophenoxy)methyl]-3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazole
- CAS Number:6148-18-1
- Molecular formula:C9H7ClN2
- Molecular Weight:178.62
6141-22-6
6148-18-1
General procedure for the synthesis of 2-(chloromethyl)quinazoline from 2-chloro-N-(2-formylphenyl)acetamide: 2-chloro-N-(2-formylphenyl)acetamide (0.869 g, 4.40 mmol) was stirred with a methanol solution of 7 N ammonia (4.4 mL, 30.8 mmol) in a sealed tube for 4.5 h at room temperature. The progress of the reaction was monitored by TLC (9:1 hexane/EtOAc) and it was found that a new point with lower Rf value was generated, but a large amount of feedstock remained unreacted. Subsequently, stirring was continued at room temperature for 19.5 hours, during which a white precipitate was formed. Volatiles were removed under reduced pressure to give a beige solid, which was treated with CHCl3. Examination of the soluble fraction of CHCl3 by TLC (7:3 hexane/EtOAc) revealed that the main component was a new point with an Rf value lower than that of the starting material. The CHCl3 solution was placed in a 0°C refrigerator for the weekend. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on an Analogix IF-280 (Agilent SF10-4g, 100% CHCl3) with the product eluting in fractions 1-10. The product-containing fractions were combined and concentrated under reduced pressure to afford 2-(chloromethyl)quinazoline as a white solid (418 mg, 53.2% yield).1H NMR (300 MHz, CDCl3) δ 9.45 (s, 1H), 8.09-8.04 (m, 1H), 7.99-7.92 (m, 2H), 7.70 (ddd, J = 8.0, 6.9 1.2 Hz, 1H), 4.92 (s, 2H).
6141-22-6
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6148-18-1
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Yield:6148-18-1 53.2%
Reaction Conditions:
with ammonia in methanol at 20; for 4.5 h;Sealed tube;
Steps:
2 Step 2:
The product of the first step, 2-chloro-N-(2-formylphenyl)acetamide (0.869 g, 4.40 mmol) and ammonia, 7N solution in methanol (4.4 mL, 30.8 mmol) were stirred together at ambient in a sealed tube for 4.5 hours. A TLC (9:1 hexane EtOAc) check indicated that a new lower Rf spot had formed, however, plenty of starting material remained so stirring at ambient temperature was continued for another 19.5 hours, during which time a white precipitate had formed. Volatiles were removed under reduced pressure to give a beige solid that was treated with CHCl3. The portion that was soluble was checked by TLC (7:3 hexane/EtOAc). The major spot in the CHCl3-soluble portion was a new one with lower Rf than the starting material. The CHCl3 mixture was placed in the 0° C. freezer over the weekend. Insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on an Analogix IF-280 (Agilent SF10-4 g, 100% CHCl3). The product eluted in fractions 1-10. The product fractions were combined and concentrated under reduced pressure to give 2-(chloromethyl)quinazoline as a white solid (418 mg, 53.2%). 1H NMR (300 MHz, CDCL3) δ 9.45 (s, 1H), 8.09 8.04 (m, 1H), 7.99-7.92 (m, 2H), 7.70 (ddd, J=8.0, 6.9, 1.2 Hz, 1H), 4.92 (s, 2H).
References:
US2013/343992,2013,A1 Location in patent:Paragraph 0302
34637-41-7
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6148-18-1
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$67.00/100mg
529-23-7
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6148-18-1
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118-92-3
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6148-18-1
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3817-05-8
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6148-18-1
56 suppliers
$67.00/100mg