Acrylonitrile → 3-((4-(2,2-Dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrophenyl)sulfonyl)-2-propenenitrile

HRID 838913Notes

Reaction equation

HRID 838913 reaction equation
[Cl:1][CH:2]([Cl:21])[C:3]([F:20])([F:19])[O:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([S:14](Cl)(=[O:16])=[O:15])=[C:7]([CH3:18])[CH:6]=1.[C:22](#[N:25])[CH:23]=[CH2:24].Cl.C(N(CC)CC)C>C(#N)C>[Cl:1][CH:2]([Cl:21])[C:3]([F:20])([F:19])[O:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([S:14]([CH:24]=[CH:23][C:22]#[N:25])(=[O:16])=[O:15])=[C:7]([CH3:18])[CH:6]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 11130Triethylamine hydrochlorideHCID 203252614-(2,2-Dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrobenzenesulfonyl chloride

Product 1

HCID 543302103-((4-(2,2-Dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrophenyl)sulfonyl)-2-propenenitrileYield 10.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 100 ml Fisher-Porter pressure vessel were placed 9.0 g (0.024 mol) of 4-(2,2-dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrobenzenesulfonyl chloride, 2.4 g (0.048 mol) acrylonitrile, 2 ml acetonitrile, 0.07 g cupric chloride and 0.12 g triethylamine hydrochloride. After cooling and evacuating the vessel to 5 mm mercury pressure, it was sealed and heated in an oil bath at 105°-110° C for 38 hours. The vessel was opened and the reaction medium was filtered with the aid of benzene. The insolubles were discarded and the filtrate was treated with 5.0 g of triethylamine, refiltered, and washed with water. After decolorizing wth charcoal and drying over MgSO4, removal of the solvent under reduced pressure afforded a dark amber oil. Recrystallization from methanol provided 1.0 g of the title compound as a white solid, m.p. 109° C.

Workup

  1. temperatureAfter cooling
  2. customevacuating the vessel to 5 mm mercury pressure, it
  3. customwas sealed
  4. temperatureheated in an oil bath at 105°-110° C for 38 hours
  5. filtrationthe reaction medium was filtered with the aid of benzene
  6. additionthe filtrate was treated with 5.0 g of triethylamine
  7. washwashed with water
  8. dry with materialdrying over MgSO4, removal of the solvent under reduced pressure
  9. customafforded a dark amber oil
  10. customRecrystallization from methanol

Sources & evidence

ORD record
ord-a5721f3dde8547abb817f25126565cce
Source dataset
uspto-grants-1978_06
Patent number
US04093644

Reaction notes

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