Acetic Acid → HCID 22402966, compound

HRID 439711Notes

Reaction equation

HRID 439711 reaction equation
[N+](=[CH2:3])=[N-].[CH:4]([C:7]1([CH3:27])[C:11](=[O:12])[NH:10][C:9]([C:13]2[C:21]3[N:20]=[C:19]([CH3:22])[N:18]([CH3:23])[C:17]=3[CH:16]=[CH:15][C:14]=2[C:24]([OH:26])=[O:25])=[N:8]1)([CH3:6])[CH3:5].C(O)(=O)C>CCOCC.CO>[CH:4]([C:7]1([CH3:27])[C:11](=[O:12])[NH:10][C:9]([C:13]2[C:21]3[N:20]=[C:19]([CH3:22])[N:18]([CH3:23])[C:17]=3[CH:16]=[CH:15][C:14]=2[C:24]([O:26][CH3:3])=[O:25])=[N:8]1)([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 22402964HCID 22402964, compound

Product 1

HCID 22402966HCID 22402966, compoundYield 28.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diazomethane in ether is added dropwise to a solution of the 4-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-1,2-dimethyl-5-benzimidazolecarboxylic acid (2.50 g, 7.61 mmol) in methanol until the yellow color persists. The reaction mixture is neutralized with acetic acid and concentrated in vacuo. Preparative HPLC (silica gel, ethyl acetate eluent) affords the title product as off-white crystals (0.750 g, 28.9%), mp 240°-242° C.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d8028051a214553827d8cb652f1e939
Source dataset
uspto-grants-1996_05
Patent number
US05516751

Reaction notes

Loading…