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

HRID 1801212ノート

反応式

HRID 1801212 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e3cee010114e4b2fa6aae90d07bb0b55
出典データセット
uspto-grants-2013_01
特許番号
US08344137B2

反応ノート

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