Ammonia → 3,3,3-Trifluoro-2,2-dimethyl-propionamide

HRID 1807702Notes

Reaction equation

HRID 1807702 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].C(C1NC=CN=1)(C1[NH:14]C=CN=1)=O.N.C(OCC)C>C(Cl)Cl>[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([NH2:14])=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 198673673,3,3-Trifluoro-2,2-dimethylpropanoic acid

Product 1

HCID 575162793,3,3-Trifluoro-2,2-dimethyl-propionamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2 g (12.81 mmol) 3,3,3-trifluoro-2,2-dimethylpropionic acid (Aldrich), 2.077 g (12.81 mmol) carbonyl-diimidazole and 5.55 ml (64.1 mmol) aqueous ammonia in 50 ml CH2Cl2 was stirred at room temperature for 20 h. After that, diethyl ether was added and the resulting mixture was washed with 0.1 N HCL, 0.1 N NaOH, water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford 1.15 g of the title compound as white crystals, that were used in the next step without further purification. MS: M+H=156.

Workup

  1. washthe resulting mixture was washed with 0.1 N HCL, 0.1 N NaOH, water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60b2759cdcc14fb2accc5b31f498f7cd
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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