Monomethyl terephthalate → 2-(4-Methoxycarbonylbenzamido)-4'-methoxyacetophenone

HRID 2270050

Reaktionsgleichung

Reaktionsgleichung von HRID 2270050
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:5].[CH3:14][O:15][C:16](=[O:26])[C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1>N1C=CC=CC=1.C(N(CC)CC)C.ClCCl>[CH3:14][O:15][C:16]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:2][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)=[O:5])=[O:22])=[CH:19][CH:18]=1)=[O:26]

Komponenten

6

Edukt 2

HCID 15513Monomethyl terephthalateHCID 124871882-Amino-4'-methoxyacetophenone hydrochloride

Produkt 1

HCID 136403692-(4-Methoxycarbonylbenzamido)-4'-methoxyacetophenoneAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4′-methoxyacetophenone hydrochloride (5.33 g) in pyridine (4.28 ml), triethylamine (3.68 ml) and dichloromethane (50 ml) was added dropwise a solution of terephthalic acid monomethyl ester (5.25 g) in dichloromethane (10 ml) at 0° C. The reaction mixture was allowed to warm to room temperature, and stirred for 3 hours. To the reaction mixture was added dichloromethane (200 ml), washed with 1N-sodium hydroxide (100 ml×2), saturated hydrogen carbonate aqueous solution (100 ml×2) and brine, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in n-hexane, and collected by filtration to give 2-(4-methoxycarbonyl-benzamido)-4′-methoxyacetophenone (7.97 g).

Aufarbeitung

  1. washwashed with 1N-sodium hydroxide (100 ml×2), saturated hydrogen carbonate aqueous solution (100 ml×2) and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-6166f9853aa6469cbc73aef21e32c70a
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331521B1

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