Methane → HCID 20342337, compound

HRID 2049538Notes

Reaction equation

HRID 2049538 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[C:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)([OH:12])=[O:11].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C>C1(C)C=CC=CC=1>[C:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[N:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:8]=[C:7]([Cl:9])[CH:6]=2)=[CH:15][CH:14]=1)([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 297MethaneHCID 120884-Formylbenzoic acidHCID 122813,5-DichloroanilineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 20342337HCID 20342337, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a reaction flask, equipped with a Dean-Stark trap, is added 3,5-dichloroaniline (16.2 g., 0.10 mole), p-carboxybenzaldehyde (0.10 moles), p-toluenesulfonic acid monohydrate (0.2 g), and toluene (100 ml.). The reaction mixture is then warmed to reflux and the water (1.65 ml.) collected by azeotroping. The cooled reaction mixture is treated with charcoal and the filtrate reduced to vacuo to give an amber oil that crystallizes on standing to give N-(p-carboxybenzylidene)-3,5-dichloroaniline which is recrystallized from pentane.

Workup

  1. customTo a reaction flask, equipped with a Dean-Stark trap
  2. temperatureThe reaction mixture is then warmed
  3. temperatureto reflux
  4. customthe water (1.65 ml.) collected
  5. customby azeotroping
  6. customThe cooled reaction mixture
  7. customto give an amber oil that
  8. customcrystallizes

Sources & evidence

ORD record
ord-c6732d636e374b8c8cc59d70b546cc57
Source dataset
uspto-grants-1980_04
Patent number
US04198349

Reaction notes

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