HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethyl Acetoacetate → Ethyl 2-(5,6-Diphenyl-1,2,4-triazin-3-yl)acetate

HRID 12564
Notes
Print preview

Reaction equation

HRID 12564 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5](C)=O.CS(C1[N:17]=[N:18][C:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1)(=O)=O>C1COCC1>[C:22]1([C:20]2[N:21]=[C:5]([CH2:4][C:3]([O:9][CH2:10][CH3:11])=[O:8])[N:17]=[N:18][C:19]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 129154813-(Methanesulfonyl)-5,6-diphenyl-1,2,4-triazine2×

Product 1

HCID 12915487Ethyl 2-(5,6-Diphenyl-1,2,4-triazin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of NaH (41 mg, 1.61 mmol) in THF (2 ml) at 0° C. was added ethyl acetoacetate (105 mg. 0.80 mmol) dropwise. After the mixture was stirred for 15 min, a solution of 3-(methylsulfonyl)-5,6-diphenyl-1,2,4-triazine (Compound 87) (250 mg, 0.80 mmol) in THF (3 ml) was cannulated into the solution, and the resulting solution was heated to 60° C. for 2 hours. The reaction was then quenched with water. The product was extracted with ethyl acetate. The organic layer was washed with water, and brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo, and the residue was purified by silica gel chromatography (20% ethyl acetate in hexane) to give title compound as a solid.

Workup

  1. customThe reaction was then quenched with water
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solvent was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b001ef4de7204123bc89d9ca3f7063f6
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728014B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes