Benzocaine → Benzoic acid, p-((3-pyridylmethylene)amino)-, ethyl ester

HRID 1801122노트

반응식

HRID 1801122 반응식
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)[CH3:2]

참가 물질

5

반응물 2

HCID 2337BenzocaineHCID 103713-Pyridinecarboxaldehyde

생성물 1

HCID 213269Benzoic acid, p-((3-pyridylmethylene)amino)-, ethyl ester수율 100.3%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A mixture of 4-amino-benzoic acid ethyl ester (33 g, 200 mmol), pyridine-3-carbaldehyde (24.0 g, 220 mmol) and p-toluenesulfonic acid (760 mg, 4 mmol) in toluene (600 mL) was heated to reflux for 12 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(pyridin-3-ylmethylene)-amino]-benzoic acid ethyl ester (51 g, quant.) as a light yellow solid: LC/MS m/e calcd for C15H14N2O2 (M+H)+: 255.29, observed: 255.4.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with ether

출처 및 근거

ORD 기록
ord-9f187d26845445e28266ae432930df55
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344137B2

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