Water → 3-[(6-Methoxy-4-chromanylidene)amino]-2-oxazolidinone

HRID 838879

Reaktionsgleichung

Reaktionsgleichung von HRID 838879
[NH2:1][N:2]1[C:6](=O)[CH2:5][O:4][CH-:3]1.[OH2:8].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH2:16][CH2:15][C:14]2=O>C1C=CC=CC=1.Cl>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH2:16][CH2:15][C:14]2=[N:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:8]

Komponenten

6

Edukt 3

HCID 962WaterHCID 46121686-methoxychroman-4-oneHCID 1785142693-amino-1,3-oxazolidin-2-id-4-one

Produkt 1

HCID 706152823-[(6-Methoxy-4-chromanylidene)amino]-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 62 g (0.61 mole) of 3-amino-2-oxazolidone in 650 ml of benzene was treated with 15 drops of HCl (isopropanol) solution using mechanical stirring, and refluxed until all water was removed via a Dean-Stark trap. The solution was then treated with 107 g (0.60 mole) of 6-methoxy-4-chromanone and refluxed for 11.5 hr. A 9.6 ml portion of water (theory: 10.8 ml) was collected. The reaction mixture was stripped of benzene under the water pump. The residue was taken up in 200 ml of 1:1 isopropanol:ether, stored 24 hr at room temperature, refrigerated overnight and filtered. The resultant cream-colored solid was washed with 125 ml of isopropanol, ether, and dried. M.p. 54°-64°; yield: 115 g (73%).

Aufarbeitung

  1. customwas removed via a Dean-Stark trap
  2. temperaturerefluxed for 11.5 hr
  3. customA 9.6 ml portion of water (theory: 10.8 ml) was collected
  4. filtrationfiltered
  5. washThe resultant cream-colored solid was washed with 125 ml of isopropanol, ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a2a0b1b410ce48e0bda49330495e0e76
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093627

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