Acetic Acid → HCID 22402966, compound

HRID 1031014Notes

Reaction equation

HRID 1031014 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, 7.6% 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-8e89762018dd4ec1b248670a410e2f42
Source dataset
uspto-grants-1992_04
Patent number
US05108485

Reaction notes

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