Water → Tilnoprofen Arbamel

HRID 1382756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1382756
[CH3:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:19][C:13]3=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=[C:12]3[CH2:11][C:10]=2[CH:20]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:27][N:28]([CH3:33])[C:29](=[O:32])[CH2:30]Cl.O>CN(C)C=O>[CH3:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:19][C:13]3=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=[C:12]3[CH2:11][C:10]=2[CH:20]=1)[C:3]([O:5][CH2:30][C:29](=[O:32])[N:28]([CH3:33])[CH3:27])=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 3080818Tilnoprofenic acid

Produkt 1

HCID 164072Tilnoprofen ArbamelAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 5.4 g of α,2-dimethyl-5H-[1]-benzopyrano [2,3-b]pyridine-7-acetic acid is dissolved in 22 ml of dimethylformamide, whereafter 1.9 g of potassium carbonate and 2.7 g of N,N-dimethyl-2-chloroacetamide are added, and the mixture is stirred at 75° C. for 2 hours. Under cooling with ice, 50 ml of water is added to the resulting reaction mixture. The precipitated crystals are collected by filtration and washed with water, and then recrystallized from isopropyl alcohol to obtain 6.4 g of N,N-dimethylcarbamoylmethyl α,2-dimethyl-5H-[1]benzopyrano[2,3-b]-pyridine-7acetate as white crystals having a melting point of 150° to 151° C.

Aufarbeitung

  1. additionare added
  2. additionis added to the resulting reaction mixture
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed with water
  5. customrecrystallized from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-bfbfe8095ec74ec293339134743d34ef
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808593

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