3-Chloropropionyl chloride → HCID 86605670, compound

HRID 2109483Notes

Reaction equation

HRID 2109483 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][CH2:27][CH2:28][C:29](Cl)=[O:30]>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:26][CH2:27][CH2:28][C:29]([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:30]

Participants

5

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 9953940Fipronil sulfide

Product 1

HCID 86605670HCID 86605670, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole (10.0 g, 19.0 mmol) in toluene was added 3-chloropropionyl chloride (3.92 g, 30.9 mmol), then zinc chloride (0.97 g, 7.1 mmol). The mixture was heated at reflux for 4 hours. After extractive workup and recrystallisation with heptane-ethyl acetate (1:1) the title product was obtained (9.05 g), 19F-NMR: −43.3; −63.7 ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customAfter extractive workup and recrystallisation with heptane-ethyl acetate (1:1) the title product
  4. customwas obtained (9.05 g), 19F-NMR: −43.3; −63.7 ppm

Sources & evidence

ORD record
ord-8ba9f4dd53a04a6cb2651eb46f0fda82
Source dataset
uspto-grants-2009_04
Patent number
US07514561B2

Reaction notes

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