HCID 19436771, compound → HCID 19436749, compound

HRID 1440155Notes

Reaction equation

HRID 1440155 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)=[CH:4][C:3]=1[S:20](Cl)(=O)=O>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)=[CH:4][C:3]=1[SH:20]

Participants

4

Reactant 1

HCID 19436771HCID 19436771, compound

Product 1

HCID 19436749HCID 19436749, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 12.8 g (0.031 mole) 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenesulfonyl chloride in 100 mL acetic acid was added 40.7 g (0.62 mole) zinc powder. The slurry was stirred at 80° C. for 4 hours, allowed to cool and filtered through Celite®. The filtrate was poured into 1.0 L water, the solid filtered and dried. The solid was recrystallized from ethanol/water to give 10.2 g (95%) of 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenethiol as a yellow solid; mp 56°-58° C.

Workup

  1. temperatureto cool
  2. filtrationfiltered through Celite®
  3. additionThe filtrate was poured into 1.0 L water
  4. filtrationthe solid filtered
  5. customdried
  6. customThe solid was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-02c698dca64e4b0aacd374c56e88b4bd
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

Loading…