Diethyl Ether → 1H-Pyrazole-4-carboxylic acid, 5-cyano-1-(1,1-dimethylethyl)-, ethyl ester

HRID 1249448Notes

Reaction equation

HRID 1249448 reaction equation
S(Cl)(Cl)=O.O[N:6]=[CH:7][C:8]1[N:12]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:11]=[CH:10][C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOCC>O>[C:7]([C:8]1[N:12]([C:13]([CH3:15])([CH3:16])[CH3:14])[N:11]=[CH:10][C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl Chloride2×HCID 1363321415-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester

Product 1

HCID 1636771H-Pyrazole-4-carboxylic acid, 5-cyano-1-(1,1-dimethylethyl)-, ethyl esterYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (6.6 ml., 0.092 mole) was added to a cold solution of 5-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester (11 grams, 0.046 mole) in 75 ml. of ether. The solution was stirred in the cold for thirty minutes, then at room temperature for 16 hours. Water was added to the reaction mixture to neutralize the remaining thionyl chloride, then the reaction mixture was poured into a separatory funnel. The phases were separated and the organic phase was washed with water and dried using sodium sulfate and filter paper. The solvent was removed in vacuo, yielding 8.5 grams of 5-cyano-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester.

Workup

  1. additionthe reaction mixture was poured into a separatory funnel
  2. customThe phases were separated
  3. washthe organic phase was washed with water
  4. customdried
  5. filtrationfilter paper
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ed6847832b214c2db8a91327742072a0
Source dataset
uspto-grants-1986_12
Patent number
US04631343

Reaction notes

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