N-Methylaniline → HCID 46871987, compound

HRID 1044055Notes

Reaction equation

HRID 1044055 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(#N)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 46871987HCID 46871987, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

N-methylaniline (2.88 ml, 26.6 mmol) was added to a solution of ethyl 2-bromo-2-phenylacetate (4.65 ml, 26.6 mmol) in acetonitrile (55 ml). The reaction was heated in sealed tube under microwave irradiation at 100° C. for 30 minutes. Acetonitrile was evaporated, residue was taken up with EtOAc and washed sequentially with 1N NaHCO3, 1N HCl and brine. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The residue was triturated with hexane and then purified by flash chromatography (Petroleum ether/EtOAc=97/3) to obtain ethyl 2-(methyl(phenyl)amino)-2-phenylacetate (4.6 g, 64.3% yield).

Workup

  1. customAcetonitrile was evaporated
  2. washwashed sequentially with 1N NaHCO3, 1N HCl and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was triturated with hexane
  7. custompurified by flash chromatography (Petroleum ether/EtOAc=97/3)

Sources & evidence

ORD record
ord-341c391af10c4de4b91f308c97e72bdd
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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