Pyridine → HCID 14852021, compound

HRID 1613269Notes

Reaction equation

HRID 1613269 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[NH2:8])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[Cl:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].C(OCC)(=O)C>CCOCC>[C:1]([C:5]1[CH:6]=[C:7]([NH:8][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][Cl:23])[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 783704-Chlorobutyryl chlorideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 14852021HCID 14852021, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
3 °C

Procedure

To a stirred mixture of 65.2 g (295 mmol) of 3,5-di-tert-butyl-4-hydroxyaniline and 23.3 g (295 mmol) of pyridine in 700 ml of ether cooled to 3° C. there was slowly added 41.6 g (295 mmol) of 4-chlorobutyryl chloride. Fifteen hours later 700 ml of ethyl acetate was added and the mixture was washed successively with 500 ml of water, 500 ml of dilute sodium bicarbonate solution and again with 500 ml of water. The organic phase was dried over anhydrous magnesium sulfate and concentrated to a solid (85.3 g). This solid was triturated in hexane and filtered to yield 75.2 g of N-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-chlorobutyramide.

Workup

  1. washthe mixture was washed successively with 500 ml of water, 500 ml of dilute sodium bicarbonate solution and again with 500 ml of water
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated to a solid (85.3 g)
  4. customThis solid was triturated in hexane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a751059130b14981a63e4174f71142b2
Source dataset
uspto-grants-1993_03
Patent number
US05192791

Reaction notes

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