Dodecylamine → N-Dodecyl difluoroacetamide

HRID 2413842Notes

Reaction equation

HRID 2413842 reaction equation
[F:1][CH:2]([F:8])[CH2:3][O:4]C(=O)C.[CH2:9]([NH2:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(NC(=O)C(F)F)CC>C(#N)C>[CH2:9]([NH:21][C:3](=[O:4])[CH:2]([F:1])[F:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 13583DodecylamineHCID 1370742,2-DifluoroethylacetateHCID 20155647N-propyl-difluoroacetamide

Product 1

HCID 20155640N-Dodecyl difluoroacetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

One equivalent difluoroethylacetate and one equivalent dodecylamine stirred at room temperature in acetonitrile 16 hours. The solvent is removed to give a white wax, which is chromatographed on silica gel in CHCl3 /EtOAc (15:1), Rf =0.7. NMR (CDCl3, δ) 7.2 b-s (1H); 5.9 g (2H) J=26; 3.35 m (2H); 1.3 s (20H); 0.9 m (3H). Other compounds prepared this way, with similar NMR, acceptable Mass Spectra and TLC: N-propyl-difluoroacetamide.

Workup

  1. customThe solvent is removed
  2. customto give a white wax, which
  3. customis chromatographed on silica gel in CHCl3 /EtOAc (15:1), Rf =0.7
  4. custom1.3 s (20H)
  5. customOther compounds prepared this way

Sources & evidence

ORD record
ord-24ea1a1594f34f08a55163949a0b894f
Source dataset
uspto-grants-1988_01
Patent number
US04719312

Reaction notes

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