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

HRID 389186ノート

反応式

HRID 389186 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2e1c966d4b20406285ea4594fddcf492
出典データセット
uspto-grants-2013_02
特許番号
US08377874B2

反応ノート

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