Water → 3-Methyl-N-phenylbut-2-enamide

HRID 1440426Notes

Reaction equation

HRID 1440426 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][C:11]([CH3:16])=[CH:12][C:13](Cl)=[O:14].O>C1COCC1>[CH3:10][C:11]([CH3:16])=[CH:12][C:13]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6115Aniline2×HCID 24758Sodium hydrideHCID 1023943-Methyl-2-butenoyl chloride2×

Product 1

HCID 123870223-Methyl-N-phenylbut-2-enamideYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round bottom flask was placed NaH (1.93 g, 0.05 mol). After washing with dry hexane (2×10 mL dry THF (15 mL) was added), to this tan solid. Then, the resulting suspension was added to a solution of aniline (Compound 36, 4.89 mL, 0.054 mol) in dry THF (7 mL) at 0° C. After stirring for 30 min, 3,3-dimethylacryloyl chloride (Compound 35, 6.56 mL, 0.059 mol) was added dropwise to the above solution. The reaction mixture was stirred under N2 for overnight followed by a slow addition of water. The mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with NH4Cl (sat.) and NaCl (sat.), dried over MgSO4 and concentrated to give the title compound as a tan solid (4.45 g, 51%). 1H NMR d 1.87 (s, 3H), 2.21 (s, 3H), 5.72 (s, 1H), 7.29-7.56 (m, 5H).

Workup

  1. customIn a 100 mL round bottom flask was placed
  2. washAfter washing with dry hexane (2×10 mL dry THF (15 mL) was added), to this tan solid
  3. stirringThe reaction mixture was stirred under N2 for overnight
  4. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  5. washThe combined organic layers were washed with NH4Cl (sat.) and NaCl (sat.)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22ea6109e0b4424a94f43bf491b0b99d
Source dataset
uspto-grants-1996_03
Patent number
US05498755

Reaction notes

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