3-Bromobenzaldehyde → 3-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester

HRID 2045491노트

반응식

HRID 2045491 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([NH2:11])[CH:5]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([N:11]=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)[CH:5]=1

참가 물질

5

반응물 2

HCID 765833-BromobenzaldehydeHCID 52987785Methyl 3-amino-5-chlorobenzoate

생성물 1

HCID 674427953-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester수율 99.7%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A mixture solution of 3-amino-5-chloro-benzoic acid methyl ester (21 g, 113.2 mmol), 3-bromo-benzaldehyde (21 g, 113.2 mmol) and p-toluenesulfonic acid (431 mg, 2.2 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 3-[(3-bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester (39.8 g, quant.) as a pale-white solid: MS calcd. for C15H11BrClNO2 353.62, obsd. (ESI+) [(M+H)+]351.9 & 353.9.

후처리

  1. temperatureto reflux for 12 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with ether

출처 및 근거

ORD 기록
ord-0fd7e7d7d1cc463a89782b89830f53c9
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586747B2

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