Triethylamine → 4,4,5,5,5-pentafluoro-N-methoxy-N-methylpentanamide

HRID 2203382Notes

Reaction equation

HRID 2203382 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:19])([C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:11][C:12](O)=[O:13].Cl.[CH3:21][NH:22][O:23][CH3:24].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[F:8][C:9]([F:19])([C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:11][C:12]([N:22]([O:23][CH3:24])[CH3:21])=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 234231634,4,5,5,5-Pentafluoropentanoic acid

Product 1

HCID 866790214,4,5,5,5-pentafluoro-N-methoxy-N-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Triethylamine (1.082 mL, 7.81 mmol) was added to a stirred solution of 4,4,5,5,5-pentafluoropentanoic acid (1.00 g, 5.21 mmol), N,O-dimethylhydroxylamine hydrochloride (0.559 g, 5.73 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.998 g, 5.21 mmol) in dry DCM (5.35 mL) at 25° C. under N2. The reaction was stirred at 25° C. overnight. The reaction was diluted with CH2Cl2 (60 mL) and washed consecutively with 1N aq. HCl (2×), satd aq. NaHCO3, dried (Na2SO4) and concentrated in vacuo to give the desired product, as a colorless liquid. 1H NMR (500 MHz, CHCl3-d): δ 3.72 (s, 3H); 3.21 (s, 3H); 2.74 (t, J=7.8 Hz, 2H); 2.51-2.37 (m, 2H). m/z=236.2 (M+H).

Workup

  1. washwashed consecutively with 1N aq. HCl (2×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c088ec25b0b348788c7ae2006710a46f
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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