p-Toluenesulfonic acid → N-(3-Phenylsalicylidene)-4-iodoaniline

HRID 1965926Notes

Reaction equation

HRID 1965926 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[C:9]([CH:10]=O)[C:8]=2[OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[C:9]([CH:10]=[N:21][C:20]3[CH:22]=[CH:23][C:17]([I:16])=[CH:18][CH:19]=3)[C:8]=2[OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 108934-IodoanilineHCID 516892Sodium BicarbonateHCID 107031002-Formyl-6-phenylphenol

Product 1

HCID 136384407N-(3-Phenylsalicylidene)-4-iodoaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An amount of 20.6 mmol of 3-phenyl salicylaldehyde (2) (4.08 g) was dissolved in 150 ml of toluene. After addition of 4-iodoaniline (5.42 g/24.8 mmol) and a few crystals of para-toluenesulfonic acid, the reaction mixture was stirred under reflux for three hours applying a Dean-Stark-trap. After cooling down to room temperature, sodium hydrogencarbonate solution (150 ml) was added. The organic phase was separated and filtered over sodium sulfate and silica. Removing the solvent and recrystallization from ethanol at −20° C. gave the title compound as a red solid. Yield: 7.25 g (88%).

Workup

  1. temperatureunder reflux for three hours
  2. customThe organic phase was separated
  3. filtrationfiltered over sodium sulfate and silica
  4. customRemoving
  5. customthe solvent and recrystallization from ethanol at −20° C.

Sources & evidence

ORD record
ord-13d2e06247df42b7b3ae7bd86573cdca
Source dataset
uspto-grants-2013_04
Patent number
US08420563B2

Reaction notes

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