Thionyl Chloride → HCID 58117230, compound

HRID 1406425Notes

Reaction equation

HRID 1406425 reaction equation
[C:1]1([C@@H:7]([N:9]2[CH:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[N:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[C:1]1([C@@H:7]([N:9]2[CH:13]=[C:12]([C:14]([Cl:19])=[O:16])[CH:11]=[N:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58117255HCID 58117255, compound

Product 1

HCID 58117230HCID 58117230, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Intermediate (6g), 1-((S)-1-Phenyl-ethyl)-1H-pyrazole-4-carboxylic acid (0.5 g, 2.31 mmol) was stirred in toluene (20 mL) at RT and thionyl chloride (0.34 mL, 4.62 mmol) was added. The reaction mixture was slowly heated to 90° C. and heating continued for 3 hrs. After cooling the reaction was concentrated in vacuo. Toluene was added to the residue and concentrated in vacuo. This was repeated a further three times and the title compound, intermediate (6h), 1-((S)-1-Phenyl-ethyl)-1H-pyrazole-4-carbonyl chloride, was isolated as an oil, 0.544 g, quantitative.

Workup

  1. temperatureheating
  2. temperatureAfter cooling the reaction
  3. concentrationwas concentrated in vacuo
  4. additionToluene was added to the residue
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-940a87bc4ef7457d95416c01dfc70beb
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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