Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate

HRID 389186노트

반응식

HRID 389186 반응식
[CH3:1][NH:2][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:16][C:17]1[CH:23]=[CH:22]C(N)=[CH:19][C:18]=1[O:24][CH3:25].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[Br:16][C:17]1[CH:23]=[CH:22][C:1]([NH:2][C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:19][C:18]=1[O:24][CH3:25]

참가 물질

5

반응물 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 70182544-Bromo-3-methoxyanilineHCID 58005139Ethyl 3-(methylamino)-3-phenylacrylate

생성물 1

HCID 58005168Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate수율 93.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the product from Step 1 (31.3 g, 152 mmol) and 4-bromo-3-methoxyaniline (28 g, 139 mmol) in DCM (700 mL) was added PPTS (38.3 g, 152 mmol). The mixture was heated to reflux with stirring for 20 hours and cooled, and the solids removed by filtration and washed with DCM. The filtrate was concentrated and purified on silica (10% to 50% DCM/hexanes) to give the title compound (49 g). LRMS (M+H)+ Calcd.: 376.0; found 376.2.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. customthe solids removed by filtration
  5. washwashed with DCM
  6. concentrationThe filtrate was concentrated
  7. custompurified on silica (10% to 50% DCM/hexanes)

출처 및 근거

ORD 기록
ord-2e1c966d4b20406285ea4594fddcf492
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377874B2

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