p-Toluenesulfonic acid → HCID 136388724, compound

HRID 1965924Notes

Reaction equation

HRID 1965924 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([CH:8]=O)[C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2].[I:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7]([CH:8]=[N:19][C:18]2[CH:20]=[CH:21][C:15]([I:14])=[CH:16][CH:17]=2)[C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 108934-IodoanilineHCID 516892Sodium BicarbonateHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 136388724HCID 136388724, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An amount of 5.84 mmol of 3-tert-butyl salicylaldehyde (1) (1.04 g/1 ml) was dissolved in 150 ml of toluene. After addition of 4-iodoaniline (1.53 g/7 mmol/1.2 equivs.) 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 sulphate and silica. Removing the solvent and recrystallization from ethanol at −20° C. gave the title compound in a 96% yield.

Workup

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

Sources & evidence

ORD record
ord-a74df035e0e849d58d78327a2e94839a
Source dataset
uspto-grants-2013_04
Patent number
US08420563B2

Reaction notes

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