Dimethyl Sulfate → 3-(4,5-Dimethoxy-2-methylaminophenyl)-2-methyl-2-propenic acid phenethyl amide

HRID 1976883Notes

Reaction equation

HRID 1976883 reaction equation
[CH2:1]([NH:9][C:10](=[O:25])[C:11]([CH3:24])=[CH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=1[NH2:23])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:26](N(CC)CC)C.S(OC)(OC)(=O)=O>CCOCC>[CH2:1]([NH:9][C:10](=[O:25])[C:11]([CH3:24])=[CH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=1[NH:23][CH3:26])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 702148893-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid phenethyl amide

Product 1

HCID 702301143-(4,5-Dimethoxy-2-methylaminophenyl)-2-methyl-2-propenic acid phenethyl amideYield 35.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a nonaqueous ether solution of 3.00 g (8.81 mmol) (E) 3-(2-amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid phenethyl amide and 1.34 ml (9.69 mmol) of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.), 0.92 ml (9.69 mmol) of dimethyl sulfate (manufactured by Wako Pure Chemical Industries, Ltd.) was slowly added dropwise. Thereafter, reflux was carried out for 2 hours at 34° C. to 35° C. After the completion of the reaction, the solvent was evaporated, and the resulting residue was dissolved in ethyl acetate. Thus obtained ethyl acetate layer was washed with water and was dried with sodium sulfate. The dried solution was concentrated under a reduced pressure, and the resulting crude product was refined by an aminopropyl-modified type silica gel column chromatography (n-hexane/ethyl acetate=1/1), whereby 1.12 g of the aimed compound was obtained as a yellowish crystal (yield: 35.9%).

Workup

  1. temperatureThereafter, reflux
  2. customAfter the completion of the reaction
  3. customthe solvent was evaporated
  4. dissolutionthe resulting residue was dissolved in ethyl acetate
  5. washThus obtained ethyl acetate layer was washed with water
  6. dry with materialwas dried with sodium sulfate
  7. concentrationThe dried solution was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-2300dac439a04419a59507765bf6f54c
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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