3-Nitrobenzaldehyde → HCID 178526623, compound

HRID 1036937Notes

Reaction equation

HRID 1036937 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13]>C1(C)C=CC=CC=1>[N+:12]([C:15]1[CH:16]=[C:17](/[CH:18]=[N:9]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=2)[CH:20]=[CH:21][CH:22]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 99644-(Trifluoromethyl)aniline

Product 1

HCID 178526623HCID 178526623, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-trifluoromethyl-phenylamine (10.0 g, 62.06 mmol) and 3-Nitro-benzaldehyde (9.3 g, 62.06 mmol) in toluene was heated to reflux for 5 h with a Dean-stark trap. After evaporation of the toluene, the reaction mixture was heated for another 1 h at this temperature to afford 18.3 g of [1-(3-nitro-phenyl)-meth-(E)-ylidene]-(4-trifluoromethyl-phenyl)-amine. The mixture was used in next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h with a Dean-stark trap
  3. customAfter evaporation of the toluene
  4. temperaturethe reaction mixture was heated for another 1 h at this temperature

Sources & evidence

ORD record
ord-07835f4c24d049d297c65fc33d5f7c16
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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