Water → Isopropyl 2-chloro-5-[(2-methoxybenzoyl)amino]benzoate

HRID 1938857

Reaktionsgleichung

Reaktionsgleichung von HRID 1938857
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:25])=[C:17]([CH:24]=1)[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.O1CCOCC1>[Cl:25][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[CH:24][C:17]=1[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 369590Isopropyl 5-amino-2-chlorobenzoate

Produkt 1

HCID 361504Isopropyl 2-chloro-5-[(2-methoxybenzoyl)amino]benzoateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Methoxybenzoyl chloride (8.8 g, 0.05 mole) was added at room temperature under a dry nitrogen atmosphere to a stirred mixture of 1-methylethyl 5-amino-2-chlorobenzoate (10.7 g, 0.05 mole), triethylamine (5.6 g, 0.055 mole) and 4-(N,N,-dimethylamino)pyridine (catalyst, 0.2 g) dissolved in dry p-dioxane (100 ml). A solid precipitate formed. Following the initial exothermic reaction (temperature increased to about 45° C.), the reaction mixture was stirred under nitrogen at room temperature for 20 hours. Next, the reaction mixture was added to water (500 ml), resulting in the precipitation of a solid product, which was collected by vacuum filtration, washed with water (500 ml), and dried to yield 16.2 g of the title compound, m.p. 94°-96° C.

Aufarbeitung

  1. customA solid precipitate formed
  2. customexothermic reaction (temperature increased to about 45° C.)
  3. customresulting in the precipitation of a solid product, which
  4. filtrationwas collected by vacuum filtration
  5. washwashed with water (500 ml)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8acb92e949dc40f08c71a3e287abe299
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05693827

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