Triethylamine → HCID 178507669, compound

HRID 1914841Notes

Reaction equation

HRID 1914841 reaction equation
[NH2:1]/[C:2](/OCC)=[CH:3]\[C:4](=O)[C:5]([F:8])([F:7])[F:6].Cl.[NH2:14][NH2:15].C(N(CC)CC)C>C(O)C>[F:6][C:5]([F:8])([F:7])[C:4]1[CH:3]=[C:2]([NH2:1])[NH:14][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115031Hydrazinium chlorideHCID 151117544-Amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 178507669HCID 178507669, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one, (Compound [XXIV]) (7.00 g, 38.2 mmol, 1.0 eq.) in ethanol (150 mL) in a 250 mL round bottom flask was added hydrazine hydrochloride (2.75 g, 40.16 mmol, 1.05 eq.) followed by triethylamine (4.05 g, 40.16 mmol, 1.05 eq.). The reaction mixture was heated to reflux for 16 hours. After cooling and concentration, the residue was purified by silica gel chromatography using CHCl3-MeOH (10%) as the eluant to give Compound [XXV]: LCMS m/e 152 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 5.32 (s, 2H) 5.51 (s, 1H) 12.12 (br. s., 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. temperatureAfter cooling
  4. concentrationconcentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-565f6522ba874b8aa693394e02a87fdf
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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