Phosphorus oxide (P4O10) → 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one

HRID 1382154

반응식

HRID 1382154 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[NH:13][NH2:14].[F:15][CH:16]([F:25])[C:17]([NH:19][C:20](=O)[O:21]CC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:20](=[O:21])[NH:19][C:17]([CH:16]([F:25])[F:15])=[N:14]1

참가 물질

5

반응물 3

HCID 14812Phosphorus oxide (P4O10)HCID 170281(2,4-Dichloro-5-(1-methylethoxy)phenyl)hydrazineHCID 14392483HCID 14392483, 화합물

생성물 1

HCID 1357451031-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one수율 48.5%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

To a stirred solution of 11.8 g (0.05 mole) of 2,4-dichloro-5-(1-methylethoxy)phenylhydrazine and 10.0 g (0.06 mole) of ethyl difluoroacetylcarbamate in 130 mL of xylene was added 2.5 g (0.02 mole) of phosphorus pentoxide. After complete addition the mixture was heated at reflux for 1.5 hours then allowed to cool to room temperature for approximately 18 hours. The reaction mixture was decanted from a dark residue in the reaction flask and washed with water. The washed mixture was extracted with a 10% aqueous sodium hydroxide solution. The basic extract was made acidic with concentrated hydrochloric acid to form an oily precipitate. This aqueous phase was decanted from the oily residue and fresh water added to wash the residue. This residue was dissolved in 160 mL of methylene chloride and filtered through a celite pad. The filtrate was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a semi-solid residue. The residue was triturated with approximately 125 mL of petroleum ether to provide 8.2 g of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one.

후처리

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureat reflux for 1.5 hours
  4. customThe reaction mixture was decanted from a dark residue in the reaction flask
  5. washwashed with water
  6. extractionThe washed mixture was extracted with a 10% aqueous sodium hydroxide solution
  7. extractionThe basic extract
  8. customto form an oily precipitate
  9. customThis aqueous phase was decanted from the oily residue and fresh water
  10. additionadded
  11. washto wash the residue
  12. dissolutionThis residue was dissolved in 160 mL of methylene chloride
  13. filtrationfiltered through a celite pad
  14. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  15. filtrationfiltered
  16. customThe filtrate was evaporated under reduced pressure
  17. customto leave a semi-solid residue
  18. customThe residue was triturated with approximately 125 mL of petroleum ether

출처 및 근거

ORD 기록
ord-4b9928f8a63d4fdfabaae0a9e8a0be4e
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04806145

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