Reaktion #9442

Reaktionsgleichung

triethyl orthoformate

Meldrum's acid

3-bromoaniline

3-bromoaniline

→

5-[(3-bromophenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to 50° C.
2. 2
   Temperaturwas maintained between 50–55° C
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGto facilitate stirring
5. 5
   workup.ADDITIONUpon complete addition
6. 6
   Temperaturthe reaction was cooled to room temperature (RT)
7. 7
   Filtrationthe solids were collected by filtration
8. 8
   WaschenThe filter cake was washed with ice cold ethanol until the washings
9. 9
   Sonstigethe product was dried at 65° C. under vacuum

Vorschrift

A mixture of triethyl orthoformate (154 grams (g), 1.04 moles (mol) and Meldrum's acid (142 g, 0.983 mol) was heated to 55° C. for 4 hours (h). After cooling to 50° C., a solution of 3-bromoaniline (162.6 g, 0.945 mol) in ethanol (300 mL) was added such that the temperature of the reaction was maintained between 50–55° C. After half of the 3-bromoaniline had been added, stirring became difficult due to the formation of solids, so more ethanol (1 liter (L)) was added to facilitate stirring. Upon complete addition, the reaction was cooled to room temperature (RT), and the solids were collected by filtration. The filter cake was washed with ice cold ethanol until the washings were nearly colorless, and the product was dried at 65° C. under vacuum to afford 287 g of 5-[(3-bromophenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione as an off-white solid.

Quelle