Diazomethane → HCID 19010332, compound

HRID 1741599Notes

Reaction equation

HRID 1741599 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]([C:13]2[NH:14][C:15]([CH:20]([CH3:22])[CH3:21])([CH3:19])[C:16](=[O:18])[N:17]=2)=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([CH3:3])=[CH2:2].[N+](=[CH2:25])=[N-]>C(Cl)Cl>[CH3:25][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:4]([C:1]([CH3:3])=[CH2:2])[CH:5]=[N:6][C:7]=1[C:13]1[NH:17][C:16](=[O:18])[C:15]([CH:20]([CH3:22])[CH3:21])([CH3:19])[N:14]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 178439584HCID 178439584, compound

Product 1

HCID 19010332HCID 19010332, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.9 g of 5-isopropenyl-2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid in 50 mL of methylene chloride, stirred at 0°, is added 60 mL of 0.25M ethereal diazomethane. After stirring for 15 minutes, the reaction is concentrated on a steam bath. The residue is chromatographed on silica gel using 2:1 ether-hexanes as eluant to afford the desired product. Recrystallization from ether-hexanes affords a solid, mp 90.5°-92.5°.

Workup

  1. concentrationthe reaction is concentrated on a steam bath
  2. customThe residue is chromatographed on silica gel using 2:1 ether-hexanes as eluant

Sources & evidence

ORD record
ord-240dadade9ff4840b1cfb6bb5e2444a1
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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