Reaktion #1067728

Reaktionsgleichung

sulfuric acid

(-)-2-amino-2,3-dimethylbutyronitrile

ammonia

→

(+)-2-amino-2,3-dimethylbutyramide

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedoes not go above 25° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   TemperaturAfter cooling the mixture in an ice-acetone bath
4. 4
   Sonstigedoes not exceed 75° C
5. 5
   ExtraktionThe mixture is extracted five times with methylene chloride
6. 6
   Sonstigethe combined extracts dried
7. 7
   Einengenconcentrated
8. 8
   SonstigeThis gives 11.95 g of white solid, mp 79°-81° C. and [α]D25 =+57.43° (c=0.0213 g/ml THF)
9. 9
   SonstigeThis solid is recrystallized from methylene chloride-hexane

Vorschrift

Concentrated sulfuric acid (29.7 ml) is cooled with stirring in an ice-acetone cooling bath. To the acid is added 11.8 g (-)-2-amino-2,3-dimethylbutyronitrile with [α]D25 =-7.31° (C=0.0368 g/ml THF) at such a rate that the temperature does not go above 25° C. After the addition, the temperature of the reaction mixture is slowly raised to 100° C. and held at that temperature for one hour. After cooling the mixture in an ice-acetone bath, 85 ml concentrated ammonia is added at such a rate that the temperature does not exceed 75° C. The mixture is extracted five times with methylene chloride, the combined extracts dried and concentrated. This gives 11.95 g of white solid, mp 79°-81° C. and [α]D25 =+57.43° (c=0.0213 g/ml THF). This solid is recrystallized from methylene chloride-hexane to give 11.2 g of (+)-2-amino-2,3-dimethylbutyramide, mp 81°-82° C. [α]D25 =+59.38° (c=0.0162 g/ml THF).

Quelle