3-Bromobenzaldehyde → 4-[(3-Bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester

HRID 2045415노트

반응식

HRID 2045415 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([Cl: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]=[CH:8][C:7]([N:10]=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)=[C:6]([Cl:11])[CH:5]=1

참가 물질

5

반응물 2

HCID 765833-BromobenzaldehydeHCID 1515284Methyl 4-Amino-3-chlorobenzoate

생성물 1

HCID 674417354-[(3-Bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester수율 99.7%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A mixture solution of 4-amino-3-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 4-[(3-bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester (39.8 g, quant.) as a pale-white solid: MS calcd. for C18H11BrClNO2 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-f51a73525c4247bd870b77fa5658b24c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586747B2

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