Mesitylene → HCID 54300158、化合物

HRID 1387529

反応式

HRID 1387529 の反応式
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

参加物

7

反応物 5

HCID 7947MesityleneHCID 8857Ethyl AcetateHCID 29766Benzene, 1-bromo-3,5-dichloro-HCID 516892Sodium BicarbonateHCID 54415798HCID 54415798、化合物

生成物 1

HCID 54300158HCID 54300158、化合物

試薬・触媒・溶媒 1

HCID 83717Copper iodide触媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-756f52fcbc6e470d8dd0e668fcf7c965
出典データセット
uspto-grants-2001_07
特許番号
US06268387B1

関連ノート

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