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

HRID 126993ノート

反応式

HRID 126993 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH2:10][CH:9]([C:11]([OH:13])=[O:12])[NH:8][N:7]=1.[C:14]([S:17][CH2:18][CH2:19][C:20](Cl)=[O:21])(=[O:16])[CH3:15]>C([O-])([O-])=O.[Na+].[Na+]>[C:14]([S:17][CH2:18][CH2:19][C:20]([N:8]1[CH:9]([C:11]([OH:13])=[O:12])[CH2:10][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:7]1)=[O:21])(=[O:16])[CH3:15]

参加物

4

反応物 2

HCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 20288723(+/-)-4,5-Dihydro-3-(2-thienyl)-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 20288729(+/-)-1-[3-(Acetylthio)-1-oxopropyl]-4,5-dihydro-3-(2-thienyl)-1H-pyrazole-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒2 回

実験手順

(±)-4,5-Dihydro-3-(2-thienyl)-1H-pyrazole-5-carboxylic acid is dissolved in aqueous Na2CO3 (1.38 g) at pH 8.6. The temperature is lowered to 5° C. and 3-(acetylthio)propionyl chloride (4.15 g) and a 25% solution of Na2CO3 are added simultaneously maintaining the pH at 8-9. The final pH is 8.9 and the reaction is stirred for 2 hours at room temperature. It is then extracted with ethyl acetate and the ethyl acetate is discarded. The aqueous layer is made strongly acid with 20% HCl and the gummy precipitate is extracted with ethyl acetate. The ethyl acetate is dried over MgSO4 and removed to yield a viscous residue (7.2 g) which is triturated with ether to yield 5.1 g of material, melting point 127°-130° C., dec. After recrystallization from CH3CN (very soluble) the melting point is constant at 134°-136° C., dec.

後処理

  1. customis lowered to 5° C.
  2. temperaturemaintaining the pH at 8-9
  3. extractionIt is then extracted with ethyl acetate
  4. extractionthe gummy precipitate is extracted with ethyl acetate
  5. dry with materialThe ethyl acetate is dried over MgSO4
  6. customremoved

出典と根拠

ORDレコード
ord-c39a2cfc81064a9c938bf2e9677cf4f5
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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