Mesitylene → HCID 54300158, 화합물

HRID 1387529

반응식

HRID 1387529 반응식
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

참가 물질

7

반응물 5

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

생성물 1

HCID 54300158HCID 54300158, 화합물

시약·촉매·용매 1

HCID 83717Copper iodide촉매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-756f52fcbc6e470d8dd0e668fcf7c965
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268387B1

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