N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2-dimethylpropanamide → HCID 21404983, compound

HRID 267872Notes

Reaction equation

HRID 267872 reaction equation
O.O.O.[I-].[Li+].C[O:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:12][C:13]=1[O:14]C>C(OCC)(=O)C.O>[OH:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][NH:18][C:19](=[O:24])[C:20]([CH3:22])([CH3:21])[CH3:23])[CH:11]=[CH:12][C:13]=1[OH:14]

Participants

4

Reactant 2

HCID 795486N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2-dimethylpropanamideHCID 23688288Lithium iodide--water (1/1/3)

Product 1

HCID 21404983HCID 21404983, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

Mix 2.2 g. of lithium iodide trihydrate and 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide, as prepared in Example 5, step A, heat under nitrogen to 180° and hold for 6 hours. Allow the melt to cool to room temperature, then dissolve the solid mixture by shaking with an ethyl acetate-water mixture. Separate the layers and wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order set forth. Dry the ethyl acetate solution over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product.

Workup

  1. additionMix 2.2 g
  2. temperatureheat under nitrogen to 180°
  3. dissolutiondissolve the solid mixture
  4. customSeparate the layers
  5. washwash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order
  6. dry with materialDry the ethyl acetate solution over anhydrous sodium sulfate
  7. filtrationfilter
  8. customevaporate to a residue
  9. customCrystallize the residue
  10. additionfrom a 9:1 mixture of toluene

Sources & evidence

ORD record
ord-db7e3958d0934dec8b7b082c84ddcb7c
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

Loading…