Water → 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester

HRID 2186452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2186452
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.CN(C)CCCN=C=NCC.[F:23][CH:24]([F:40])[O:25][C:26]1[C:31]2[N:32]=[C:33]([CH2:35][CH3:36])[O:34][C:30]=2[C:29]([C:37](O)=[O:38])=[CH:28][CH:27]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:37]([C:29]2[C:30]3[O:34][C:33]([CH2:35][CH3:36])=[N:32][C:31]=3[C:26]([O:25][CH:24]([F:23])[F:40])=[CH:27][CH:28]=2)=[O:38])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224566434-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid

Produkt 1

HCID 545360974-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl esterAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

para-Nitrophenol (0.95 g), 4-dimethylaminopyridine (80 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.4 g) were added to a stirred suspension of 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (1.6 g) in dry dichloromethane (60 ml) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 18 hours. Water (20 ml) was added and the aqueous layer extracted with dichloromethane (400 ml). The organic layer was washed with water (80 ml), separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 1:4 ethyl acetate/heptane to 1:1:2 ethyl acetate/dichloromethane/heptane afforded the title compound as a pale yellow solid (1.9 g)

Aufarbeitung

  1. extractionthe aqueous layer extracted with dichloromethane (400 ml)
  2. washThe organic layer was washed with water (80 ml)
  3. customseparated
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customPurification by column chromatography on silica eluting with 1:4 ethyl acetate/heptane to 1:1:2 ethyl acetate/dichloromethane/heptane

Quellen und Nachweise

ORD-Eintrag
ord-0114594b9977408cbf1a918894fd76f9
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403791B1

Notizen zur Reaktion

Wird geladen…