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

HRID 2045696Notes

Reaction equation

HRID 2045696 reaction equation
CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH3:18][NH:19][C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[Br:33][C:34]1[CH:40]=[CH:39]C(N)=[CH:36][C:35]=1[O:41][CH3:42]>C(Cl)Cl>[Br:33][C:34]1[CH:40]=[CH:39][C:18]([NH:19][C:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:36][C:35]=1[O:41][CH3:42]

Participants

5

Reactant 3

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

Product 1

HCID 58005168Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PPTS (38.3 g, 152 mmol) was added 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). The mixture was heated to reflux and stirred for 20 h. The mixture was cooled, and the solids were removed by filtration and washed with DCM. The filtrate was concentrated and purified on silica gel (gradient elution 10% to 50% DCM in hexanes) to give the title compound (49 g, 94% yield). LRMS (M+H)+ Calcd.: 376.0; found 376.2.

Workup

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

Sources & evidence

ORD record
ord-119390963e3a4e00bf6763ce47cc9b00
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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