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

HRID 389186Notes

Reaction equation

HRID 389186 reaction equation
[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]

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 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2e1c966d4b20406285ea4594fddcf492
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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