Potassium Carbonate → N-but-3-en-1-yl-N-(4-methoxyphenyl)acrylamide

HRID 564383Notes

Reaction equation

HRID 564383 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].C([O-])([O-])=O.[K+].[K+].[C:20](Cl)(=[O:23])[CH:21]=[CH2:22]>C(Cl)Cl>[CH2:1]([N:5]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[C:20](=[O:23])[CH:21]=[CH2:22])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13140Acryloyl chlorideHCID 44131193N-but-3-en-1-yl-4-methoxyaniline

Product 1

HCID 67004663N-but-3-en-1-yl-N-(4-methoxyphenyl)acrylamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-but-3-en-1-yl-4-methoxyaniline (340 mg, 1.92 mmol) in methylene chloride (5 mL) was added K2CO3 (530 mg, 3.80 mmol) and acryloyl chloride (234 μL, 2.88 mmol) at 0° C. After 15 min., the reaction was quenched with NaHCO3 (2 mL, sat. aq.) and the organic layer was isolated, concentrated and subjected to flash chromatography (Hexanes:EtOAc 4:1) to yield N-but-3-en-1-yl-N-(4-methoxyphenyl)acrylamide (395 mg, 89%).

Workup

  1. customthe reaction was quenched with NaHCO3 (2 mL, sat. aq.)
  2. customthe organic layer was isolated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8acc044da1214e2d9d48fc7f8e5af148
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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