Benzocaine → Ethyl 4-[(1-oxoallyl)amino]benzoate

HRID 388177

Reaction equation

HRID 388177 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH2:6]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)[CH3:7].C(N(CC)CC)C>ClCCl>[CH2:6]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:12][CH:11]=1)[CH3:7]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 84618Ethyl 4-[(1-oxoallyl)amino]benzoateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of acryloyl chloride (1.08 mL, 13.32 mmol) in dry dichloromethane (10 mL) was slowly added dropwise, via addition funnel, a solution of 4-aminobenzoic acid ethyl ester (2.0 g, 12.11 mmol) and triethylamine (1.86 mL, 13.32 mmol) in dry dichloromethane (5 mL) over about 30 minutes. The reaction was stirred at room temperature for 16 hours. The solution was then partitioned between dichloromethane and water in a separatory funnel. The organic layer was washed with 2 N HCl, dried with sodium sulfate, and concentrated in vacuo to dryness. The resulting residue was triturated with hexane, and vacuum filtered to yield 2.02 g (76%) of 4-acryloylaminobenzoic acid ethyl ester as a solid.

Workup

  1. customThe solution was then partitioned between dichloromethane and water in a separatory funnel
  2. washThe organic layer was washed with 2 N HCl
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo to dryness
  5. customThe resulting residue was triturated with hexane, and vacuum
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ab53dde7c8244dce9ce2350fe271f1c0
Source dataset
uspto-grants-2013_02
Patent number
US08377456B2

Linked notes

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