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

HRID 388177

反応式

HRID 388177 の反応式
[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]

参加物

5

反応物 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 13140Acryloyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab53dde7c8244dce9ce2350fe271f1c0
出典データセット
uspto-grants-2013_02
特許番号
US08377456B2

関連ノート

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