Ammonia → 2-Amino-2,3-dimethylbutanamide

HRID 2119229Notes

Reaction equation

HRID 2119229 reaction equation
[NH2:1][C:2]([CH3:8])([CH:5]([CH3:7])[CH3:6])[C:3]#[N:4].C1C[O:12]CC1.S(=O)(=O)(O)O.N>C(Cl)Cl>[NH2:1][C:2]([CH3:8])([CH:5]([CH3:7])[CH3:6])[C:3]([NH2:4])=[O:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 943552-Amino-2,3-dimethylbutyronitrile

Product 1

HCID 97937732-Amino-2,3-dimethylbutanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g of (-)-2-amino-2,3-dimethylbutyronitrile, [α]D =-6.71° (c=0.03307 g/ml THF) in 10 ml methylene chloride is added with stirring at 80° C. to 13.95 g of concentrated sulfuric acid. The solution is heated for one hour, allowed to cool and 14 g of ice is added. Next, 27 ml of concentrated ammonia is added while cooling. The resulting solution is extracted with methylene chloride (5×25 ml). The combined extracts are dried and evaporated to dryness to afford 3.23 g of title product, mp 81°-83° C., [α]D =+53.04° (c =0.0313 g/ml THF).

Workup

  1. temperatureThe solution is heated for one hour
  2. temperatureto cool
  3. temperaturewhile cooling
  4. extractionThe resulting solution is extracted with methylene chloride (5×25 ml)
  5. customThe combined extracts are dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-637bcc3741f24f8ca89442e30704822b
Source dataset
uspto-grants-1987_07
Patent number
US04683324

Reaction notes

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