Pyridine → 3-Butyl-6-(3,5-di-tert-butyl-4-hydroxybenzamido)-phthalide

HRID 2120192Notes

Reaction equation

HRID 2120192 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:33]=[C:32]2[C:27]([CH:28]([CH2:34][CH2:35][CH2:36][CH3:37])[O:29][C:30]2=[O:31])=[CH:26][CH:25]=1.N1C=CC=CC=1>CCOCC>[CH2:34]([CH:28]1[C:27]2[C:32](=[CH:33][C:24]([NH:23][C:8](=[O:10])[C:7]3[CH:11]=[C:12]([C:15]([CH3:17])([CH3:16])[CH3:18])[C:13]([OH:14])=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=3)=[CH:25][CH:26]=2)[C:30](=[O:31])[O:29]1)[CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 24386Thionyl ChlorideHCID 98777066-Amino-3-butyl-phthalide

Product 1

HCID 234391063-Butyl-6-(3,5-di-tert-butyl-4-hydroxybenzamido)-phthalide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.50 g (10 mmol) of 3,5-di-tert-butyl-4-hydroxy-benzoic acid are heated with 2.5 ml of thionyl chloride under reflux for 30 minutes. The reaction mixture is evaporated in vacuo and the residue is mixed with petroleum ether to remove the excess of thionyl chloride. 2.05 g (10 mmol) of compound obtained in Example 4 are mixed with 8.6 g of dry pyridine and dried ether. To this suspension there is added, dropwise, the ethereal solution of acyl chloride prepared above; the reaction mixture is refluxed for 30 minutes. The solvents are removed in vacuo. The residue is washed with water and dried. The title compound is crystallised from ethyl acetate.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe reaction mixture is evaporated in vacuo
  3. additionthe residue is mixed with petroleum ether
  4. customto remove the excess of thionyl chloride
  5. additionTo this suspension there is added
  6. temperaturethe reaction mixture is refluxed for 30 minutes
  7. customThe solvents are removed in vacuo
  8. washThe residue is washed with water
  9. customdried
  10. customThe title compound is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-1ff1f5d0a5e9418ea86b31bae4da0983
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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