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

HRID 126989Notes

Reaction equation

HRID 126989 reaction equation
[O: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]>O.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[O:1][CH:5]=[CH:4][CH:3]=2)=[N:7]1)=[O:21])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 20288730(+/-)-3-(2-Furanyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

Product 1

HCID 20288734(+/-)-1-[3-(Acetylthio)-1-oxopropyl]-3-(2-furanyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acidYield 58.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent2×

Procedure

(±)-3-(2-Furanyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (4.5 g) is dissolved in 200 cc of water containing 1.38 g of sodium carbonate (pH 9.4) at 10° C. 3-(Acetylthio)propionyl chloride (4.15 g) and 20% sodium carbonate solution are added simultaneously maintaining the pH between 8.5 and 9.4 and the temperature at 10° C. The final reaction mixture (pH 9.7) is stirred at room temperature for 2 hours and extracted with ethyl acetate (discarded) and the aqueous layer made strongly acid with 20% HCl. A precipitate forms which is extracted into ethyl acetate immediately. The solvent is dried and removed to yield 4.5 g of crystalline material which cannot be recrystallized.

Workup

  1. temperaturemaintaining the pH between 8.5 and 9.4
  2. customat 10° C
  3. extractionextracted with ethyl acetate (discarded)
  4. extractionA precipitate forms which is extracted into ethyl acetate immediately
  5. customThe solvent is dried
  6. customremoved

Sources & evidence

ORD record
ord-01dca90412b844f6ae01aa61a3717e2d
Source dataset
uspto-grants-1981_03
Patent number
US04254267

Reaction notes

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