Toluene → 2-(3,5-ditert-butyl-4-hydroxy-benzoyl)-3-dimethylamino-N-methyl-prop-2-enamide

HRID 2039750Notes

Reaction equation

HRID 2039750 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[CH2:4][C:5]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=1)=[O:6].C1(C)C=CC=CC=1.CO[CH:32](OC)[N:33]([CH3:35])[CH3:34]>CO>[CH3:1][NH:2][C:3](=[O:22])[C:4](=[CH:32][N:33]([CH3:35])[CH3:34])[C:5]([C:7]1[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]([OH:17])=[C:11]([C:13]([CH3:14])([CH3:15])[CH3:16])[CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 866627063-(3,5-DI-Tert-butyl-4-hydroxyphenyl)-N-methyl-3-oxopropanamide

Product 1

HCID 866627082-(3,5-ditert-butyl-4-hydroxy-benzoyl)-3-dimethylamino-N-methyl-prop-2-enamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100-mL round bottom flask was charged with 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-3-oxo-propanoic acid methyl amide (3.05 mg, 10 mmol) and toluene (20 mL). The mixture was heated and to the resulting hot solution was added N,N-dimethylformamide dimethyl acetal (1.50 mL, 11.3 mmol) with evolution of methanol. The mixture was stirred for 5 h without further heating then evaporated to an oil that was taken up in ethyl acetate (50 mL). The resulting solution was washed with water (4×50 mL) then with brine (20 mL), dried with sodium sulfate and evaporated to an oil and then further dried to a solid foam that was kept under high vacuum to reach a constant weight, then ground to a fine powder to afford 3.55 g of the title compound (98%). TLC (ethyl acetate) Rf 0.09. This material, and especially the equivalent material derived from N,N-dimethylacetamidine dimethyl acetal, is readily hydrolyzed to the starting material. It is therefore advisable to use the condensation product directly and immediately after solvent removal.

Workup

  1. temperatureThe mixture was heated and to the resulting hot solution
  2. temperaturewithout further heating
  3. customthen evaporated to an oil that
  4. washThe resulting solution was washed with water (4×50 mL)
  5. dry with materialwith brine (20 mL), dried with sodium sulfate
  6. customevaporated to an oil
  7. customfurther dried to a solid foam that

Sources & evidence

ORD record
ord-5cdaaa7bd2614079a56cfba609dcb574
Source dataset
uspto-grants-2013_11
Patent number
US08580805B2

Reaction notes

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