Dimethylamine → 3,5-di(t-butyl)-4-hydroxy-N,N-dimethylbenzamide

HRID 65724

Reaction equation

HRID 65724 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](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].ClCCl.S(Cl)(Cl)=O.[CH3:26][NH:27][CH3:28]>CN(C)C=O>[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]([N:27]([CH3:28])[CH3:26])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6344DichloromethaneHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 143003063,5-di(t-butyl)-4-hydroxy-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 25 g. (0.1 mole) of 3,5-di(t-butyl)-4-hydroxybenzoic acid in 200 ml. of dichloromethane is added 1 ml. of N,N-dimethylformamide and 0.11 mole of thionyl chloride. The mixture is heated at its reflux temperature for 40 minutes, then 0.1 mole of aqueous dimethylamine is added dropwise. The mixture is stirred for three hours and extracted twice with dichloromethane. The dichloromethane extracts are dried then evaporated to provide a residue which is recrystallized from a benzene-hexane mixture. The while solid is dissolved in dichloromethane, washed twice with 10 percent sodium hydroxide solution, then the dichloromethane layer is evaporated under vacuum. The product is recrystallized twice from a benzene-hexane mixture to provide 3,5-di(t-butyl)-4-hydroxy-N,N-dimethylbenzamide, m.p. 173°-174.5° C.

Workup

  1. temperatureThe mixture is heated at its
  2. temperaturereflux temperature for 40 minutes
  3. extractionextracted twice with dichloromethane
  4. dry with materialThe dichloromethane extracts are dried
  5. customthen evaporated
  6. customto provide a residue which
  7. customis recrystallized from a benzene-hexane mixture
  8. dissolutionThe while solid is dissolved in dichloromethane
  9. washwashed twice with 10 percent sodium hydroxide solution
  10. customthe dichloromethane layer is evaporated under vacuum
  11. customThe product is recrystallized twice from a benzene-hexane mixture

Sources & evidence

ORD record
ord-1aec26faf9514b71909f6b994b08426d
Source dataset
uspto-grants-1978_12
Patent number
US04128664

Linked notes

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