2-Chloropropionyl chloride → 5-(2-Chloropropionylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

HRID 2109482Notes

Reaction equation

HRID 2109482 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].[Cl:26][CH:27]([CH3:31])[C:28](Cl)=[O:29]>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:26][CH:27]([CH3:31])[C:28]([NH:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23])=[O:29]

Participants

5

Reactant 2

HCID 1110192-Chloropropionyl chlorideHCID 9953940Fipronil sulfide

Product 1

HCID 866056695-(2-Chloropropionylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole (8.0 g, 19.0 mmol) in toluene was added 2-chloropropionyl chloride (3.62 g, 28.5 mmol), then zinc chloride (0.77 g, 5.7 mmol). The mixture was heated at reflux for 16 hours. After extractive workup and recrystallisation with heptane-ethyl acetate (1:1) the title product was obtained (7.02 g), 19F-NMR: −43.7; −64.2 ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customAfter extractive workup and recrystallisation with heptane-ethyl acetate (1:1) the title product
  4. customwas obtained (7.02 g), 19F-NMR: −43.7; −64.2 ppm

Sources & evidence

ORD record
ord-d1c753d891c347b5929010114f8bf184
Source dataset
uspto-grants-2009_04
Patent number
US07514561B2

Reaction notes

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