4-Chlorobenzaldehyde → HCID 136332414, compound

HRID 2400264Notes

Reaction equation

HRID 2400264 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>O.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:8][CH:7]=3)[N:1]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 697392-Amino-4-(trifluoromethyl)benzamide

Product 1

HCID 136332414HCID 136332414, compound

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 962WaterSolvent

Procedure

To a stirred suspension of 2-amino-4-(trifluoromethyl)benzamide (33.6 g, 0.16 mol) in water (750 mL) was added dropwise 4-chlorobenzaldehyde. Iron trichloride hexahydrate (133 g) was then added in portions. The reaction mixture was then heated at reflux for 24 h. After allowing the suspension to cool to room temperature, the precipitate was isolated by vacuum filtration washing with water (3×500 mL) and dried under vacuum (10 mbar, 50° C.). Yield=50 g, 94%; HPLC-mass spectrometry (LC-MS): 3.7 min, 325 (M+).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 24 h
  3. customthe precipitate was isolated by vacuum filtration
  4. washwashing with water (3×500 mL)
  5. customdried under vacuum (10 mbar, 50° C.)
  6. custom3.7 min, 325 (M+)

Sources & evidence

ORD record
ord-3b8ceb7c0ee94b25a4d0257f0dc80bd9
Source dataset
uspto-grants-2014_08
Patent number
US08796180B2

Reaction notes

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