Reaktion #66988

ord-87e5fe62015a43dd8ee41f09b19d01e6

Reaktionsgleichung

Cc1ccccc1N1C(=O)CS/C1=N\C(C)C
3-(2-methylphenyl)-2-[(Z)-isopropylimino]-thiazolidin-4-one
O=Cc1ccc2c(c1)OCCO2
2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde
CC(=O)[O-].[Na+]
sodium acetate
→
Cc1ccccc1N1C(=O)/C(=C/c2ccc3c(c2)OCCO3)S/C1=N\C(C)C
5-(2,3-dihydro-benzo[1,4]dioxin-6-ylmeth-(Z)-ylidene)-2-[(Z)-isopropylimino]-3-o-tolyl-thiazolidin-4-one

Edukte

Cc1ccccc1N1C(=O)CS/C1=N\C(C)C
3-(2-methylphenyl)-2-[(Z)-isopropylimino]-thiazolidin-4-one
O=Cc1ccc2c(c1)OCCO2
2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde
CC(=O)[O-].[Na+]
sodium acetate

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeHPLC purification
  2. 2
    workup.ADDITIONThe product containing fractions
  3. 3
    Sonstigeare evaporated
  4. 4
    Sonstigedried

Vorschrift

A solution of 3-(2-methylphenyl)-2-[(Z)-isopropylimino]-thiazolidin-4-one (50 mg, 0.200 mmol), 2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde (49 mg, 0.300 mmol) and sodium acetate (33 mg, 0.400 mmol) in acetic acid (1 mL) is stirred at 110° C. for 5 h. The reaction mixture is cooled to rt and subjected to prep. HPLC purification. The product containing fractions are evaporated and dried to give 5-(2,3-dihydro-benzo[1,4]dioxin-6-ylmeth-(Z)-ylidene)-2-[(Z)-isopropylimino]-3-o-tolyl-thiazolidin-4-one.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524752B2uspto-grants-2013_09