Dimethylformamide → 1,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde

HRID 1851096ノート

反応式

HRID 1851096 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9](=[O:18])[N:8]1[CH3:19].[OH-].[Na+].CN([CH:25]=[O:26])C>O>[CH3:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([CH:25]=[O:26])[C:9](=[O:18])[N:8]1[CH3:19]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 155598371,2-Dimethyl-5-phenyl-1,2-dihydro-3H-pyrazol-3-one

生成物 1

HCID 583683381,2-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

N,N-Dimethylformamide (3.4 mL, 43.6 mmol) was added to a flask under nitrogen atmosphere. After cooling to 0° C., phosphorus oxychloride (1.4 mL, 15.2 mmol) was added. The resulting reaction mixture was stirred at room temperature for 50 minutes. The resulting reaction mixture was transferred to a reaction flask containing a solution of 1,2-dimethyl-5-phenyl-1H-pyrazol-3(2H)-one (820 mg, 4.36 mmol) in DMF (4.9 mL). The reaction flask was immersed in a preheated oil bath (120° C.) and, after stirring for 12 minutes, cooled to room temperature. 5 N NaOH (15 mL) was added to the cooled reaction mixture. After diluting with icy water, the mixture was extracted with chloroform. The organic layer was dried with sodium sulfate and then filtered. The filtrate was concentrated. After diluting DMF remaining in the resulting residue again with chloroform and then washing with water, the aqueous layer was extracted again with chloroform. The organic layer was collected, dried with sodium sulfate, and then filtered. The filtrate was concentrated. The concentrated residue was subjected to the next step without further purification.

後処理

  1. customThe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. customwas transferred to a reaction flask
  4. customThe reaction flask was immersed in a preheated oil bath
  5. stirring(120° C.) and, after stirring for 12 minutes
  6. temperaturecooled to room temperature
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. additionAfter diluting DMF remaining in the resulting residue again with chloroform
  12. washwashing with water
  13. extractionthe aqueous layer was extracted again with chloroform
  14. customThe organic layer was collected
  15. dry with materialdried with sodium sulfate
  16. filtrationfiltered
  17. concentrationThe filtrate was concentrated
  18. customThe concentrated residue was subjected to the next step without further purification

出典と根拠

ORDレコード
ord-e4dbb6a91ea24352be8ad73e2d9d4b58
出典データセット
uspto-grants-2015_02
特許番号
US08957102B2

反応ノート

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