3,3-Dimethylbutanoyl chloride → N-(5-Bromo-2-{[2-(trifluoromethoxy)ethyl]amino}phenyl)-3,3-dimethylbutanamide

HRID 1817899Notes

Reaction equation

HRID 1817899 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH:8][CH2:9][CH2:10][O:11][C:12]([F:15])([F:14])[F:13])=[CH:6][CH:7]=1.[C:17]([CH2:21][C:22](Cl)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][O:11][C:12]([F:13])([F:15])[F:14])=[C:4]([NH:16][C:22](=[O:23])[CH2:21][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]=1

Participants

4

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 688709884-Bromo-N1-[2-(trifluoromethoxy)ethyl]benzene-1,2-diamine

Product 1

HCID 68873554N-(5-Bromo-2-{[2-(trifluoromethoxy)ethyl]amino}phenyl)-3,3-dimethylbutanamideYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-bromo-N1-[2-(trifluoromethoxy)ethyl]benzene-1,2-diamine (step B, 752 mg, 2.51 mmol) in ethyl acetate (22 mL) was added tert-butylacetyl chloride (355 mg, 2.64 mmol) at room temperature. After stirring for 2 h at room temperature, the mixture was diluted with ethyl acetate. The organic solution was washed with saturated sodium hydrogencarbonate aqueous solution, brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 as eluent) to afford the title compound (728 mg, 73%) as a white solid.

Workup

  1. washThe organic solution was washed with saturated sodium hydrogencarbonate aqueous solution, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 as eluent)

Sources & evidence

ORD record
ord-6f94ec8b22fc47a6bec37fbfdfe7b04d
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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