Triethylamine → N-(4-fluorophenyl)prop-2-enamide

HRID 1582750Notes

Reaction equation

HRID 1582750 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9](Cl)(=[O:12])[CH:10]=[CH2:11].C(N(CC)CC)C>O1CCCC1>[C:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:12])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 13140Acryloyl chloride

Product 1

HCID 3250203N-(4-fluorophenyl)prop-2-enamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluoroaniline (7 ml) and acryloyl chloride (7.2 ml) were dissolved in tetrahydrofuran (100 ml), then triethylamine (15 ml) was added thereto, and the mixture was stirred overnight at room temperature. The organic layer was partitioned by adding aqueous saturated sodium bicarbonate and ethyl acetate, and the organic layer was washed with water and dried over sodium sulfate anhydrous, and after the drying agent was filtered off, the filtrate was evaporated, whereby the title compound (12.2g, 100%) was obtained as pale yellow solid.

Workup

  1. customThe organic layer was partitioned
  2. additionby adding aqueous saturated sodium bicarbonate and ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over sodium sulfate anhydrous
  5. filtrationafter the drying agent was filtered off
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e0bbd3078ba7473eaa022dca29988c67
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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