Thionyl Chloride → HCID 86650204, compound

HRID 1406420Notes

Reaction equation

HRID 1406420 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12](O)=[O:13])[CH:9]=[N:8]2)=[CH:4][CH:3]=1.FC1C=CC(CN2C=C(C(O)=O)C=N2)=CC=1.S(Cl)([Cl:35])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]([Cl:35])=[O:13])[CH:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 196200321006452-67-0HCID 43565332HCID 43565332, compound

Product 1

HCID 86650204HCID 86650204, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

1-(4-Methyl-benzyl)-1H-pyrazole-4-carboxylic acid (0.618 g, 2.86 mmol), which had been prepared according to the protocol described for intermediate (6e), in Example 21, was stirred in toluene (20 mL) at RT and thionyl chloride (681 mg, 0.42 mL, 5.72 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 crude solid obtained was triturated using isohexane. The solids were separated by filtration washed with isohexane and dried in vacuo to afford 1-(4-methyl-benzyl)-1H-pyrazole-4-carbonyl chloride as a white solid, 0.67 g, quant.

Workup

  1. temperatureheating
  2. temperatureAfter cooling the reaction
  3. concentrationwas concentrated in vacuo
  4. additionToluene was added to the residue
  5. concentrationconcentrated in vacuo
  6. customthe crude solid obtained
  7. customwas triturated
  8. customThe solids were separated by filtration
  9. washwashed with isohexane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-87c384e2a8304abdab9dc93ef907696a
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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