Trifluoroacetic acid → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-formylphenyl)acrylamide

HRID 735169Notes

Reaction equation

HRID 735169 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:36])/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([CH:31](OC)[O:32]C)=[CH:27][CH:26]=3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>C(Cl)(Cl)Cl.O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:36])/[CH:23]=[CH:24]/[C:25]3[CH:26]=[CH:27][C:28]([CH:31]=[O:32])=[CH:29][CH:30]=3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68819697(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-dimethoxymethylphenyl)acrylamide

Product 1

HCID 86601892(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-formylphenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent2×

Procedure

70 mL of water and 21 mL of trifluoroacetic acid are added to a suspension of 9.8 g (24.02 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-dimethoxymethylphenyl)acrylamide in 280 mL of chloroform and the reaction mixture is stirred for 8 hours at ambient temperature. It is diluted with chloroform and water, the organic phase is separated off and extracted with water. The organic phase is dried, filtered through silica gel, and the solvent is distilled off. Yield: 5.5 g; C22H16ClNO2 (M=361.83); calc.: molecular ion peak (M+H)+: 362/364; found: molecular ion peak (M+H)+: 362/364; Rf value: 0.6 (silica gel, cyclohexane/ethyl acetate (1:1)).

Workup

  1. customthe organic phase is separated off
  2. extractionextracted with water
  3. customThe organic phase is dried
  4. filtrationfiltered through silica gel
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-f3f23132980c40bbb6fe53683a7d8269
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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