Acetic Anhydride → (4Z)-4-(4-Cyclopropylbenzylidene)-2-[4-(2-cyclopropylethoxy)phenyl]-1,3-oxazol-5(4H)-one

HRID 456277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456277
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH:20]1([C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=C(\NC(=O)C3C=CC(OCCC4C=CC(OC)=CC=4)=CC=3)/C(NCCO)=O)=[CH:25][CH:24]=2)[CH2:22][CH2:21]1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O.CCCCCC>[CH:20]1([C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=[C:14]3\[N:13]=[C:11]([C:10]4[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH:1]5[CH2:2][CH2:3]5)=[CH:19][CH:18]=4)[O:17][C:15]\3=[O:16])=[CH:25][CH:24]=2)[CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 57684552N-((Z)-2-(4-Cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)-4-[2-(4-methoxyphenyl)ethoxy]benzamideHCID 66812105N-[4-(2-Cyclopropylethoxy)benzoyl]glycine

Produkt 1

HCID 66812352(4Z)-4-(4-Cyclopropylbenzylidene)-2-[4-(2-cyclopropylethoxy)phenyl]-1,3-oxazol-5(4H)-oneAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of N-[4-(2-cyclopropylethoxy)benzoyl]glycine (184 mg, 0.699 mmol) prepared in Example 9 (9b), 4-cyclopropylbenzaldehyde (113 mg, 0.769 mmol) prepared in Example 5, sodium acetate (75 mg, 0.909 mmol), and acetic anhydride (660 μL, 6.99 mmol) was stirred at 120° C. for 30 minutes and was then allowed to cool to room temperature. Hexane (2 mL) and water (4 mL) were added to the resulting solidified product which was washed by ultrasonic vibration. The precipitate was collected by filtration, washed with water and hexane, and dried by heating under reduced pressure to give 196 mg of the title compound (white powder, yield: 74%).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwas washed by ultrasonic vibration
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and hexane
  5. customdried
  6. temperatureby heating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b78bb6c0b3a74c9aaf6813d44e2afd66
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497397B2

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