3-(Acetylsulfanyl)propanoyl chloride → (+/-)-1-[3-(Acetylthio)-1-oxopropyl]-3-(2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

HRID 127000ノート

反応式

HRID 127000 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[NH:9][N:8]=1.[C:15]([S:18][CH2:19][CH2:20][C:21](Cl)=[O:22])(=[O:17])[CH3:16]>O.C(=O)(O)[O-].[Na+].CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>[C:15]([S:18][CH2:19][CH2:20][C:21]([N:9]1[CH:10]([C:12]([OH:14])=[O:13])[CH2:11][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8]1)=[O:22])(=[O:17])[CH3:16]

参加物

7

反応物 2

HCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 20288728(+/-)-3-(2-Pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 20288727(+/-)-1-[3-(Acetylthio)-1-oxopropyl]-3-(2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 10340Sodium Carbonate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

(±)-3-(2-Pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (3.82 g) is dissolved in 100 ml of water containing 2.12 g of sodium bicarbonate at 10° C. 3-(Acetylthio)propionyl chloride (3.9 g) in 15 ml of ether and 20% sodium carbonate solution are added simultaneously; the pH is maintained between 7.5 and 8.5. The reaction mixture is then stirred at room temperature for 2 hours and extracted with ether (discarded). The aqueous layer is acidified with acetic acid and extracted with ethyl acetate three times. The solvent is dried over anhydrous magnesium sulfate and concentrated in vacuo, yielding the title compound.

後処理

  1. temperaturethe pH is maintained between 7.5 and 8.5
  2. extractionextracted with ether (discarded)
  3. extractionextracted with ethyl acetate three times
  4. dry with materialThe solvent is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e320229640d249138174d2cb033f71cd
出典データセット
uspto-grants-1981_03
特許番号
US04254267

反応ノート

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