Diazomethane → HCID 22402972, compound

HRID 1463206Notes

Reaction equation

HRID 1463206 reaction equation
[N+](=[CH2:3])=[N-].[CH2:4]([N:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:30]([OH:32])=[O:31])=[C:19]([C:20]3[NH:21][C:22](=[O:29])[C:23]([CH:26]([CH3:28])[CH3:27])([CH3:25])[N:24]=3)[C:14]=2[N:13]=[C:12]1[CH3:33])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCOCC.CO>[CH2:4]([N:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:30]([O:32][CH3:3])=[O:31])=[C:19]([C:20]3[NH:21][C:22](=[O:29])[C:23]([CH:26]([CH3:28])[CH3:27])([CH3:25])[N:24]=3)[C:14]=2[N:13]=[C:12]1[CH3:33])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 22402976HCID 22402976, compound

Product 1

HCID 22402972HCID 22402972, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diazomethane in ether is added to a suspension of 1-benzyl-4-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-2-methyl-5-benzimidazolecarboxylic acid (1.15 g, 2.84 mmol) in methanol until the yellow color persists The reaction is stirred for 5 minutes, quenched with 2 drops of acetic acid and concentrated in vacuo. The resultant residue is purified by HPLC (silica gel, ethyl acetate eluent) to give the title product as a white powder (0.480 g, 40.3%), mp 194°-196° C.

Workup

  1. customquenched with 2 drops of acetic acid
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue is purified by HPLC (silica gel, ethyl acetate eluent)

Sources & evidence

ORD record
ord-be02f2c4aa8e45bcbab813aa3dbac9d5
Source dataset
uspto-grants-1994_04
Patent number
US05300479

Reaction notes

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