Hydrochloric Acid → 4-(4-Bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carbonyl Chloride

HRID 257563Notes

Reaction equation

HRID 257563 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:8]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:9][N:10]([C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=3[Cl:24])[C:11]=2[C:12](O)=[O:13])=[C:4]([F:31])[CH:3]=1.S(Cl)([Cl:34])=O.Cl>C1CCCCC1>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:8]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:9][N:10]([C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=3[Cl:24])[C:11]=2[C:12]([Cl:34])=[O:13])=[C:4]([F:31])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 197832084-(4-bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 197831954-(4-Bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture of 672 mg (1.32 mmol) of 4-(4-bromo-2-fluorobenzyl)-3-n-butyl-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carboxylic acid (from Step C), 2.3 mL of thionyl chloride, and 6 mL of cyclohexane was stirred at reflux under N2 for 4 hours, during which time HCl gas was evolved. The cooled solution was concentrated in vacuo to yield an orange oil, which was used directly in the next step.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customto yield an orange oil, which

Sources & evidence

ORD record
ord-9b9b18b85b29407482b7fd4f764cf79a
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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