Carbon Tetrachloride → 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole

HRID 573394

반응식

HRID 573394 반응식
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C(O[C:26](=[N:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:27])C>O>[CH3:27][C:26]1[N:28]=[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:10])[N:9]=1

참가 물질

6

반응물 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 13028604Ethyl (1E)-N-benzoylethanimidate

생성물 1

HCID 580684593-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole수율 84%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Next, into a 300-mL recovery flask were put 8.68 g of o-tolylhydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N), and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in Step 1 above was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and the aqueous layer was subjected to extraction with chloroform. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptzl-mp) (an orange oily substance, 84% yield). A synthesis scheme of Step 2 is shown in (a-2) below

후처리

  1. customNext, into a 300-mL recovery flask were put
  2. extractionthe aqueous layer was subjected to extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. additionadded
  6. filtrationThe obtained mixture was gravity-filtered
  7. concentrationthe filtrate was concentrated
  8. customto give an oily substance
  9. customThe obtained oily substance was purified by silica gel column chromatography
  10. concentrationThe obtained fraction was concentrated

출처 및 근거

ORD 기록
ord-ddd45484f0914af79feb01ae0ca144cc
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029558B2

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