Ammonia → Fenpiclonil

HRID 620956Notes

Reaction equation

HRID 620956 reaction equation
C([N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])[C:6]([C:17](F)(F)F)=[CH:5]1)(=O)C.[NH3:21]>O1CCOCC1>[Cl:16][C:10]1[C:11]([Cl:15])=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:6]([C:17]#[N:21])=[CH:5][NH:4][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21245533N-Acetyl-4-(2,3-dichlorophenyl)-3-trifluoromethylpyrrole

Product 1

HCID 91724Fenpiclonil

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.4 g of N-acetyl-4-(2,3-dichlorophenyl)-3-trifluoromethylpyrrole, 15 ml of 25% aqueous ammonia solution and 60 ml of dioxane are stirred for 18 hours at 160° C. in an autoclave. The reaction mixture is cooled to room temperature and filtered, and the clear filtrate is concentrated by evaporation. The viscous residue is dissolved in ethyl acetate; the solutiion is washed firstly with water and then with a diluted sodium chloride solution; it is subsequently dried over sodium sulfate, filtered, and concentrated by evaporation. To the residue is added n-hexane, and the crystals which precipitate are filtered off and dried. The yield is 5.3 g of 4-(2,3-dichlorophenyl)-3-cyanopyrrole, m.p. 149°-150° C.

Workup

  1. filtrationfiltered
  2. concentrationthe clear filtrate is concentrated by evaporation
  3. dissolutionThe viscous residue is dissolved in ethyl acetate
  4. washthe solutiion is washed firstly with water
  5. dry with materialit is subsequently dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. additionTo the residue is added n-hexane
  9. filtrationthe crystals which precipitate are filtered off
  10. customdried

Sources & evidence

ORD record
ord-61c863adc8624c1db47f39a7d6f04b12
Source dataset
uspto-grants-1989_04
Patent number
US04822919

Reaction notes

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