Pyridine → 3-ethoxy-N-(4-iodo-phenyl)-acrylamide

HRID 1295444Notes

Reaction equation

HRID 1295444 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:15]([O:17][CH:18]=[CH:19][C:20](Cl)=[O:21])[CH3:16]>C(Cl)Cl>[CH2:15]([O:17][CH:18]=[CH:19][C:20]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)=[O:21])[CH3:16]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 108934-IodoanilineHCID 30144293-Ethoxy-2-propenoyl chloride2×

Product 1

HCID 541035893-ethoxy-N-(4-iodo-phenyl)-acrylamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of 4-iodoaniline (14 g, 64 mmol) and pyridine (10.5 mL, 128 mmol) in methylene chloride (85 mL) was added 3-ethoxy-acryloyl chloride (10 g, 75 mmol). After stirring for 5 hrs, more 3-ethoxy-acryloyl chloride (5 g, 38 mmol) and pyridine (10.5 mL, 64 mmol) was added. After stirring for 2 days, the reaction mixture was washed with water 3×100 mL), dried over MgSO4 and concentrated to give 3-ethoxy-N-(4-iodo-phenyl)-acrylamide as black oil (11.32 g, 56%). LC-MS m/e 318 (MH+).

Workup

  1. stirringAfter stirring for 2 days
  2. washthe reaction mixture was washed with water 3×100 mL),
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-164662d58ef746f583e8aa4b20948ce9
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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