Carbon Tetrachloride → HCID 71073431, compound

First, 7.4 g of 3-bromophenyl hydrazine hydrochloride and 80 mL of carbon tetrachloride were put into a 200-mL three-neck flask, 3.5 g of triethylamine (Et3N) was added dropwise to this mixture little by little, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.8 g of N-(1-ethoxybenzylidene)butyramide obtained in Step 1 of Synthesis Example 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After the stirring, this mixture was dissolved in chloroform and washed with water and saturated saline. After the washing, anhydrous magnesium sulfate was added to the organic layer for drying. This mixture was gravity-filtered, and the obtained filtrate was concentrated to give an oily substance. This oily substance was purified by silica gel column chromatography. As the developing solvent, dichloromethane was used. The obtained fraction was concentrated to give a solid. This solid was recrystallized with a mixed solvent of toluene and hexane to give 1-(3-bromophenyl)-3-phenyl-5-propyl-1H-1,2,4-triazole (white powder, 47% yield). The synthesis scheme of Step 1 is shown in (E-1) below.

1. additionwas added to this mixture
2. stirringthe mixture was stirred at room temperature for 24 hours
3. washwashed with water and saturated saline
4. additionAfter the washing, anhydrous magnesium sulfate was added to the organic layer
5. customfor drying
6. filtrationThis mixture was gravity-filtered
7. concentrationthe obtained filtrate was concentrated
8. customto give an oily substance
9. customThis oily substance was purified by silica gel column chromatography
10. concentrationThe obtained fraction was concentrated
11. customto give a solid
12. customThis solid was recrystallized with a mixed solvent of toluene and hexane

ORD record

ord-7de7c24d65b443b0b0511ee8d2cd8272

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09406894B2