Triethylamine → 2-(p-Chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carbonitrile

HRID 129647

Reaction equation

HRID 129647 reaction equation
[F:1][C:2]([S:5][C:6](Cl)=[N:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)([F:4])[F:3].Cl[C:18](=[CH2:21])[C:19]#[N:20].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[NH:7][C:6]([S:5][C:2]([F:4])([F:3])[F:1])=[CH:21][C:18]=2[C:19]#[N:20])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 18930385Trifluoromethyl 1-chloro-N-(p-chlorobenzyl)thioformimidate

Product 1

HCID 189303922-(p-Chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carbonitrileYield 57.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen purge, a solution of trifluoromethyl-1-chloro-N-(p-chlorobenzyl)thioformimidate (1.1 g, 0.004 mol) and 2-chloroacrylonitrile (0.4 mL, 0.005 mol) is treated with a solution of triethylamine (1.3 mL, 0.009 mol) in toluene. After an induction period, solids begin to form as the reaction mixture exotherms slightly. When the exotherm subsides, the reaction mixture is heated at reflux temperature for 16 hours, cooled and filtered. The filter cake is washed with ethyl acetate and the filtrate is concentrated in vacuo to obtain a semi-solid. The semi-solid is dissolved in ethyl acetate and the organic solution is washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. The solid is twice recrystallized from 1,2-dichloroethane to give the title product as a beige solid (0.7 g, mp 203°-205° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. customUnder a nitrogen purge
  2. customto form as the reaction mixture
  3. temperatureWhen the exotherm subsides, the reaction mixture is heated
  4. temperatureat reflux temperature for 16 hours
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe filter cake is washed with ethyl acetate
  8. concentrationthe filtrate is concentrated in vacuo
  9. customto obtain a semi-solid
  10. washthe organic solution is washed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customto obtain a solid
  14. customThe solid is twice recrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-a099147a108340039e6a16d88b514b47
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Linked notes

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