1,3,5-Triazine → HCID 18329937, compound

HRID 2271096Notes

Reaction equation

HRID 2271096 reaction equation
[Na].[O:2]=[C:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N:18]1[CH:23]=NC=N[CH:19]=1>C(O)C>[CH2:11]([C:10]1[C:3](=[O:2])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:23][NH:18][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 92621,3,5-TriazineHCID 61162Ethyl 3-oxo-5-phenylpentanoateHCID 5360545Sodium

Product 1

HCID 18329937HCID 18329937, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium (0.5835 g, 25.4 mmol) in ethanol (18 ml) under nitrogen, was added ethyl 3-oxo-5-phenylpentanoate (5.5752 g, 25.3 mmol) in ethanol (5 ml) and 1,3,5-triazine (2.0544 g, 25.3 mmol). The mixture was heated at reflux for 1 h, then allowed to cool. The solvent was removed in vacuo, and water (15 ml) was added to the residue. The pH was brought to 4 by the addition of concd HCl (3 ml) and the mixture was left overnight. The resulting solid was collected by filtration, washed with ethanol and dried under vacuum at 60° C. to yield 4.6324 g (71%) of the title compound as a buff solid; 1H NMR (360 MHz, DMSO-d6) δ1.24 (3H, t, J 7.1 Hz), 3.64 (2H, s), 4.16 (2H, q, J 7.1 Hz), 7.15-7.28 (5H, m), 7.53 (1H, s), 8.18 (1H, s), 11.64 (1H, br s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureto cool
  4. customThe solvent was removed in vacuo, and water (15 ml)
  5. additionwas added to the residue
  6. additionThe pH was brought to 4 by the addition of concd HCl (3 ml)
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with ethanol
  9. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-7d82a7d1838d4dd48e6163a6e9ac57e7
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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