Ammonia → 2-Amino-2,3-dimethylbutanamide

HRID 1650104Notes

Reaction equation

HRID 1650104 reaction equation
S(=O)(=O)(O)[OH:2].[NH2:6][C:7]([CH3:13])([CH:10]([CH3:12])[CH3:11])[C:8]#[N:9].N>C1COCC1>[NH2:6][C:7]([CH3:13])([CH:10]([CH3:12])[CH3:11])[C:8]([NH2:9])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 943552-Amino-2,3-dimethylbutyronitrile

Product 1

HCID 97937732-Amino-2,3-dimethylbutanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

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]25D =-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 wih 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°0 (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°L C. [α]D25 =+59.38° (c=0.0162 g/ml THF).

Workup

  1. customdoes not go above 25° C
  2. additionAfter the addition
  3. temperatureAfter cooling the mixture in an ice-acetone bath
  4. customdoes not exceed 75° C
  5. extractionThe mixture is extracted five times wih methylene chloride
  6. customthe combined extracts dried
  7. concentrationconcentrated
  8. customThis solid is recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-3cefdca2f1bb4c2d8c60eadb2999ae38
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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