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

HRID 77026노트

반응식

HRID 77026 반응식
[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]

참가 물질

5

반응물 3

HCID 6115Aniline2회HCID 81531DiisopropylethylamineHCID 59401272Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8545127f95aa4575b0973415b8ec7e40
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

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