Carbon Tetrachloride → HCID 24975976, compound

First, 14 g of phenyl hydrazine hydrochloride and 200 ml, of carbon tetrachloride were put into a 500-mL three-neck flask, 30 mL of triethylamine (Et3N) was added dropwise to the mixture little by little, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 17 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, toluene was used. The obtained fraction was concentrated, so that 1,3-diphenyl-5-propyl-1H-1,2,4-triazole (abbreviation: HPrp3tz1-Ph) was obtained (a red oily substance, 29% yield). The synthesis scheme of Step 1 is shown in (C-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, so that 1,3-diphenyl-5-propyl-1H-1,2,4-triazole (abbreviation: HPrp3tz1-Ph)
11. customwas obtained (a red oily substance, 29% yield)
12. customThe synthesis scheme of Step 1

ORD record

ord-7fcf5906837144869045166030619095

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09406894B2