Mesitylene → 3-[Acetyl-(3,5-dichlorophenyl)-amino]-4-methoxybenzoic acid methyl ester

HRID 1859680Notes

Reaction equation

HRID 1859680 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8]C(OC)=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14].Br[C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=1.[C:26](=O)(O)[O-:27].[Na+].C1(C)C=C(C)C=C(C)C=1.[C:40]([O:43][CH2:44]C)(=[O:42])[CH3:41]>[Cu](I)I>[CH3:44][O:43][C:40](=[O:42])[C:41]1[CH:8]=[CH:9][C:4]([O:27][CH3:26])=[C:5]([N:12]([C:13](=[O:15])[CH3:14])[C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[CH:6]=1

Participants

7

Reactant 5

HCID 7947MesityleneHCID 8857Ethyl AcetateHCID 29766Benzene, 1-bromo-3,5-dichloro-HCID 516892Sodium BicarbonateHCID 54415798Methyl 2-acetamido-4-methoxybenzoate

Product 1

HCID 543001583-[Acetyl-(3,5-dichlorophenyl)-amino]-4-methoxybenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

A mixture of 2-acetylamino-4-methoxybenzoic acid methyl ester (9.58 g, 42.92 mmol), 1-bromo-3,5-dichlorobenzene (28.80 g, 127.48 mmol), copper iodide (2.32 g, 12.18 mmol), and sodium bicarbonate (8.72 g, 103.80 mmol) in of mesitylene (60 mL) was heated to reflux. After 7 days, the mixture was allowed to cool and was diluted with ethyl acetate (300 mL). The resulting solid was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel eluting with hexane/ethyl acetate (9:1<1:1) to afford the product (11.6 g); m.p. 100-101° C. after trituration in hexane.

Workup

  1. temperaturewas heated to reflux
  2. temperatureto cool
  3. customThe resulting solid was removed by filtration
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (9:1<1:1)

Sources & evidence

ORD record
ord-20dbf901c6bc490195330f212ccb382a
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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