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

HRID 1882905Notes

Reaction equation

HRID 1882905 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-c2456356902f4395a385612bbd72032c
Source dataset
uspto-grants-2004_07
Patent number
US06759427B2

Reaction notes

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