Carbaryl synthesis
- Product Name:Carbaryl
- CAS Number:63-25-2
- Molecular formula:C12H11NO2
- Molecular Weight:201.22
123-39-7
90-15-3
63-25-2
General procedure for the synthesis of metanaphthoate from N-methylformamide and 1-naphthol: Cu(OAc)2 (20 mol%) and 1,10-phenanthroline (20 mol%) were added in a reaction vessel and dissolved in 2 mL of formamide. After stirring the reaction mixture for 5 minutes, 1-naphthol substrate was added. Subsequently, TBHP (5-6 M in decane solution) was slowly added dropwise to the reaction mixture and stirring was continued for 5 minutes. The reaction system was warmed up to 80°C with continuous stirring for 8 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was purified directly by silica gel column chromatography, using a solvent mixture of 5-10% ethyl acetate and hexane for elution, to obtain the target product, methenazone (3). Special attention should be paid during the column chromatographic separation, as the raw material and the product have similar Rf values on TLC, they need to be monitored in combination with UV and iodine vapor chromatography. For the reaction of N-methylformamide, slightly modified conditions were used: the reaction was carried out at room temperature for 2 hours. The crude product was purified directly by silica gel column chromatography to give the target product (5).
Yield:63-25-2 82%
Reaction Conditions:
with tert.-butylhydroperoxide;4,7-dimethoxy-1,10-phenanthroline;iron(II) bromide in decane at 20; for 2 h;Inert atmosphere;
Steps:
General procedure for the synthesis
General procedure: In a reaction vessel, 2ml of formamide was added to the phenol substrate and the solutionwas stirring over a period of 1 minute. On stirred add 5 mmol% of Iron (II)Bromide, and 5 mmol% 4,7-Dimethoxy- 1,10 phenanthroline to the above reaction mixture,then slowly add 3 mmol of TBHP (Oxidant) at room temperature. Then, raise thetemperature up to 60 C and allow the stirring for 4 hours under an inert atmosphere inpresence of molecular sieves. After completion of reaction time, the solvent wasremoved under reduced pressure or directly proceeded for the conventional work upwith ethyl acetate, water mixture. The organic layer was separated and dried overanhydrous Na2SO4. Removal of the solvent under reduced pressure afforded the crudeproduct, which was purified by column chromatography on silica gel using hexane andethyl acetate (8:2) mixture to afford the required product (3). TLC’s have to be monitoredby both UV and iodine
References:
Vala, Manoj Kumar;Sudhakar, Chithaluri;Adurthi, Suryakumari;Vanam, Shekhar [Synthetic Communications,2022,vol. 52,# 2,p. 250 - 257]
90-15-3
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124-38-9
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63-25-2
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$39.00/100mg
105-40-8
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90-15-3
743 suppliers
$9.00/5g
63-25-2
266 suppliers
$39.00/100mg
