Triethylamine → HCID 86714664, compound

HRID 1409451Notes

Reaction equation

HRID 1409451 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][C:4](=[N:6][OH:7])[NH2:5].CCN(CC)CC.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[C:18]#[CH:19]>C(#N)C>[NH2:5][C:4](=[N:6][O:7][CH:19]=[CH:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])[CH2:3][C:2]([F:9])([F:8])[F:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12182Ethyl propiolateHCID 57368850HCID 57368850, compound

Product 1

HCID 86714664HCID 86714664, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

Into a flask containing 3,3,3-trifluoro-N′-hydroxypropanimidamide (21 mmol, 3 g) in ACN (50 ml), Et3N (21 mmol, 3.5 ml) was added at RT. The resulting mixture was heated at 80° C. and a solution of ethyl propiolate (25.1 mmol, 2.5 g) in ACN (20 ml) was added. The reaction mixture was heated at 80° C. for overnight. The solvent was evaporated and the crude was purified by flash-chromatography. Yield 3.8 g. 1H-NMR (400 MHz; DMSO-d6): δ 1.17 (t, 3H), 3.18 (q, 2H), 4.09 (q, 2H), 5.44 (d, 1H), 6.78 (bs, 2H), 7.70 (d, 1H). LC-MS: [M−1]=239.17.

Workup

  1. additionwas added at RT
  2. temperatureThe reaction mixture was heated at 80° C. for overnight
  3. customThe solvent was evaporated
  4. customthe crude was purified by flash-chromatography

Sources & evidence

ORD record
ord-24be4673625745e4bf3f13c52839f276
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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