Sulfuric Acid → 2-Amino-2,3-dimethylbutanamide
Reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]([CH3:13])([CH:10]([CH3:12])[CH3:11])[C:8]#[N:9].[OH-:14].[NH4+]>C1COCC1>[NH2:6][C:7]([CH3:13])([CH:10]([CH3:12])[CH3:11])[C:8]([NH2:9])=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To concentrated sulfuric acid (29.7 ml), cooled with stirring in an ice-acetone cooling bath, 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 ammonium hydroxide 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).
Workup
- customdoes not go above 25° C
- additionAfter the addition
- temperatureAfter cooling the mixture in an ice-acetone bath
- customdoes not exceed 75° C
- extractionThe mixture is extracted five times with methylene chloride
- customthe combined extracts dried
- concentrationconcentrated
- customThis gives 11.95 g of white solid, mp 79°-81° C. and [α]D25 =+57.43° (c=0.0213 g/ml THF)
- customThis solid is recrystallized from methylene chloride-hexane
Sources & evidence
- ORD record
- ord-22a9597f7c25497b92d4f0a40a5380cc
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04439607
Reaction notes
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