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

HRID 561254

반응식

HRID 561254 반응식
[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]

참가 물질

5

반응물 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 13140Acryloyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cf2f30ab7a2742ee8453ac143b7493ce
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063233B2

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