Pyridine → O-(3,5-Di-tert-butyl-4-hydroxybenzoyl)-N,N-dibenzylhydroxylamine

HRID 703700

Reaction equation

HRID 703700 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:23]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:35]=1[OH:36])[C:30](Cl)=[O:31])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:37]([C:34]1[CH:33]=[C:29]([CH:28]=[C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:35]=1[OH:36])[C:30]([O:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:31])([CH3:40])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69297DibenzylhydroxylamineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 14875965O-(3,5-Di-tert-butyl-4-hydroxybenzoyl)-N,N-dibenzylhydroxylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 27.9 g of dibenzylhydroxylamine and 10.3 g of pyridine in 100 ml of methylene chloride is added a solution of 39.0 g of 3,5-di-tert-butyl-4-hydroxybenzoyl chloride in 100 ml of methylene chloride. After stirring the mixture at room temperature for 24 hours, the reaction mixture is washed with 10% aqueous hydrochloric acid, water, brine and dried. Evaporation followed by crystallization of the residue from heptane affords the title compound as a white solid: mp 90°-92° C.

Workup

  1. washthe reaction mixture is washed with 10% aqueous hydrochloric acid, water, brine
  2. customdried
  3. customEvaporation
  4. customfollowed by crystallization of the residue from heptane

Sources & evidence

ORD record
ord-ab569101f6a242b6984bdd51bb502d75
Source dataset
uspto-grants-1991_01
Patent number
US04983770

Linked notes

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