Trifluoroacetic anhydride → HCID 12641099, compound

HRID 1504967Notes

Reaction equation

HRID 1504967 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([NH2:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]#[N:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 106798654-(4-nitrophenyl)butanamide

Product 1

HCID 12641099HCID 12641099, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 81 (3.2 g, 22.4 mmol) in DCM (60 mL) was added TEA (10 mL, 77 mmol) at room temperature with stirring. Then to the mixture was added dropwise TFAA (4 mL, 30.8 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 h. Then the mixture was diluted with DCM, washed by water and brine, dried over Na2SO4 and concentrated to dryness to give compound 82 (2.7 g, 93%) as a yellow oil. 1H NMR (400 MHz, CDCl3) 8.12 (d, 2H, J=8.1 Hz), 7.30 (d, 2H, J=8.1 Hz), 2.85 (t, 2H, J=7.5 Hz), 2.31 (t, 2H, J=7.3 Hz), 1.92-2.05 (m, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 h
  2. washwashed by water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1d1b7bfb44534f09b33558ae12446aea
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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