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

HRID 1247555Notes

Reaction equation

HRID 1247555 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 (11). 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 (11)
  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-2e5bc1b8082d4bd0a55f436329751d2c
Source dataset
uspto-grants-2006_10
Patent number
US07129270B2

Reaction notes

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