2,3,4-Trifluorobenzoyl chloride → N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamide

HRID 548683Notes

Reaction equation

HRID 548683 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Si:13]([O:20][CH2:21][CH2:22][NH:23][CH3:24])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl.[OH-].[Na+]>[CH3:19][C:16]([Si:13]([CH3:14])([CH3:15])[O:20][CH2:21][CH2:22][N:23]([CH3:24])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 27340222,3,4-Trifluorobenzoyl chlorideHCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

Product 1

HCID 57663171N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,3,4-trifluoro-N-methylbenzamideYield 82.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2,3,4-Trifluorobenzoyl chloride (2.32 mL, 18.16 mmol) was added slowly to a stirred mixture of (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)methylamine (3.44 g, 18.16 mmol) in DCM (200 mL) and 10% aqueous sodium hydroxide solution (200 mL) at 0° C. The reaction was allowed to warm to RT and stirred for a further 24 hours. The phases were separated and the aqueous phase further extracted with DCM (3×100 mL), the combined organics dried (MgSO4), filtered and the solvent removed in vacuo to give a pale yellow oil. The residue was chromatographed on silica, eluting with 0-50% ethyl acetate in isohexane, to give the desired compound as a colourless oil (5.22 g).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase further extracted with DCM (3×100 mL)
  3. dry with materialthe combined organics dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give a pale yellow oil
  7. customThe residue was chromatographed on silica
  8. washeluting with 0-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-5a58a21ddba2451fa62ea92ba1d304c8
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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