Toluene → Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate

HRID 1819732

반응식

HRID 1819732 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.O=[C:13]([CH2:19][CH3:20])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C1(C)C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:13]([CH2:19][CH3:20])=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 1140TolueneHCID 99644-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerate

생성물 1

HCID 68545758Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate수율 75.8%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 962Water용매

실험 절차

In a 2L-flask were placed 4-trifluoromethylaniline (161 g, 1.00 mol), methyl 3-oxopentanoate (143 g, 1.10 mol) and toluene (640 ml). To this solution was added p-toluenesulfonic acid monohydrate (3.2 g, 0.017 mol), and the resulting mixture was heated in a bath kept at 100° C. under a reduced pressure of 27 kPa, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. After 15 hours, the heating was discontinued, nitrogen leaked in, and the reaction mixture cooled. The solvent was evaporated by means of a rotary-evaporator, and the residue was distilled under reduced pressure to give 207 g of the title compound. The yield was 75.8%.

후처리

  1. temperaturethe resulting mixture was heated in a bath
  2. temperatureunder reflux
  3. temperaturecooled
  4. customThe solvent was evaporated by means of a rotary-evaporator
  5. distillationthe residue was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-fbf8b10172544378a5bf05e890f84571
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601842B2

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