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

Ethyl Acetate → HCID 178441743, compound

HRID 53044
Notes
Print preview

Reaction equation

HRID 53044 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:12]#N)=[C:8]([C:10]#[N:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:14]([Mg]Cl)([CH3:17])([CH3:16])[CH3:15].C(OCC)(=[O:22])C.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.C(OCC)C>[CH2:1]([C:5]1[NH:9][C:8]([C:10]#[N:11])=[C:7]([C:12](=[O:22])[C:14]([CH3:17])([CH3:16])[CH3:15])[N:6]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 52605912-butyl-1H-imidazole-4,5-dicarbonitrileHCID 178418310HCID 178418310, compound

Product 1

HCID 178441743HCID 178441743, compound

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.4 g of 2-butylimidazole-4,5-dicarbonitrile (prepared as described in Preparation 1) in 150 ml of methylene chloride was added dropwise in an atmosphere of nitrogen at 10°-15° C. to 100 ml of a 2M solution of t-butylmagnesium chloride in diethyl ether, and the mixture was stirred at the same temperature for 1 hour. 200 ml of ethyl acetate and 100 ml of aqueous potassium hydrogensulfate were then added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 20 minutes. At end of this time, insoluble materials were removed by filtration, and the organic layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:3 by volume mixture of ethyl acetate and hexane as the eluent, to give 7.95 g of the title compound as crystals, melting at 135°-137° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. customAt end of this time, insoluble materials were removed by filtration
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-aa1f18992e28478093bd1ea50e0c87ae
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616599

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes