Triethylamine → 2-Butenamide, N-(4-fluorophenyl)-3-methyl-

HRID 1374617Notes

Reaction equation

HRID 1374617 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](O)=[O:5].ClC(OCC)=O.C(N(CC)CC)C.[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>C1COCC1.O>[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 10928Ethyl chloroformateHCID 109313-Methyl-2-butenoic acid

Product 1

HCID 5320912-Butenamide, N-(4-fluorophenyl)-3-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (0.1 mol) of 3-methyl-2-butenoic acid in 200 ml of THF is mixed with 9.4 ml (0.1 mol) of ethyl chloroformate and 14.1 ml (0.1 mol) of triethylamine at 0° C. After 10 minutes at room temperature, 10.6 ml (0.11 mol) of 4-fluoroaniline is added to it. The batch is stirred for 1 hour at room temperature, diluted with water and extracted with ethyl acetate (1 l). The organic phase is washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is purified by column chromatography on silica gel with hexane-ethyl acetate. Yield 18.8 g.

Workup

  1. extractionextracted with ethyl acetate (1 l)
  2. washThe organic phase is washed with saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is purified by column chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-569ab97148bb46ae9d801ea3d11b03ce
Source dataset
uspto-grants-2007_01
Patent number
US07166592B2

Reaction notes

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