Mesitylene → HCID 54300158, compound

HRID 1387529

Reaction equation

HRID 1387529 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 54415798HCID 54415798, compound

Product 1

HCID 54300158HCID 54300158, compound

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-756f52fcbc6e470d8dd0e668fcf7c965
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Linked notes

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