Aniline → Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

HRID 77026ノート

反応式

HRID 77026 の反応式
[CH2:1]([O:3][C:4](=[O:21])[CH:5](OS(C)(=O)=O)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2]

参加物

5

反応物 3

HCID 6115Aniline2 回HCID 81531DiisopropylethylamineHCID 59401272Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

生成物 1

HCID 59401228Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester収率 60%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester (I102) (594 mg, 1.82 mmol), aniline (0.25 mL, 2.73 mmol), and DIPEA (0.48 mL, 2.73 mmol) are dissolved in acetonitrile (4 mL). The reaction is heated under microwave irradiation at 100° C. for 1 hour and 30 minutes. Aniline (0.17 mL, 1.820 mmol) is added again and the reaction is heated under microwave irradiation at 100° C. for 3 hours. Acetonitrile is removed under vacuum and the residue is purified by flash chromatography (Petroleum ether/DCM=75/25) to afford intermediate I151 as a yellow oil (195 mg, 60% yield).

後処理

  1. temperaturethe reaction is heated under microwave irradiation at 100° C. for 3 hours
  2. customAcetonitrile is removed under vacuum
  3. customthe residue is purified by flash chromatography (Petroleum ether/DCM=75/25)

出典と根拠

ORDレコード
ord-8545127f95aa4575b0973415b8ec7e40
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

反応ノート

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