Ammonia → Fenpiclonil

HRID 247103

Reaction equation

HRID 247103 reaction equation
F[C:2](F)(F)[C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[CH:6][NH:5][CH:4]=1.[NH3:18]>O1CCOCC1>[Cl:15][C:9]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:3]([C:2]#[N:18])=[CH:4][NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 212455323-Trifluoromethyl-4-(2,3-dichlorophenyl)-pyrrole

Product 1

HCID 91724Fenpiclonil

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.0 g of 3-trifluoromethyl-4-(2,3-dichlorophenyl)-pyrrole, 21 ml of 25% aqueous ammonia and 40 ml of dioxane are stirred for 26 hours at 180° C. in an autoclave. After cooling to room temperature, the reaction mixture is filtered, and the clear filtrate is concentrated by evaporation. The residue is taken up in ethyl acetate, washed with water and subsequently with diluted sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue is caused to crystallise by the addition of hexane; it is then filtered off and dried to thus obtain 3.4 g (100% of theory) of 4-(2,3-dichlorophenyl)-3-cyanopyrrole having a melting point of 150° C.

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationthe clear filtrate is concentrated by evaporation
  3. washwashed with water and subsequently with diluted sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customto crystallise by the addition of hexane
  8. filtrationit is then filtered off
  9. dry with materialdried to thus obtain 3.4 g (100% of theory) of 4-(2,3-dichlorophenyl)-3-cyanopyrrole having a melting point of 150° C.

Sources & evidence

ORD record
ord-35c8aa3adda7435983b40f361ae24f35
Source dataset
uspto-grants-1987_11
Patent number
US04705801

Linked notes

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