2-Methyl-2-butene → 4,5-diethyl-1H-imidazole-2-carboxylic acid

HRID 43489Notes

Reaction equation

[CH2:1]([C:3]1[N:4]=[C:5]([CH:10]=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9])[CH3:2].Cl([O-])=[O:13].[Na+].P([O-])(O)(O)=O.[Na+].CC(=CC)C>>[CH2:8]([C:7]1[N:6]=[C:5]([C:10]([OH:13])=[O:11])[NH:4][C:3]=1[CH2:1][CH3:2])[CH3:9]

Participants

Reactant 4

HCID 105532-Methyl-2-butene

HCID 23668197Sodium Chlorite

HCID 23672064Monosodium phosphate

HCID 866485014,5-Diethyl-1H-imidazole-2-carbaldehyde

Product 1

HCID 684062254,5-diethyl-1H-imidazole-2-carboxylic acidYield 9.4%

Procedure

The same operation as in Example (33c) was performed using 4,5-diethyl-1H-imidazole-2-carbaldehyde obtained in Example (43b) (352 mg, 2.31 mmol), sodium chlorite (420 mg, 4.64 mmol), sodium dihydrogenphosphate (725 mg, 4.64 mmol) and 2-methyl-2-butene (1 mL, 9.45 mmol), to obtain 36.7 mg of the title compound as a white solid (9.4%).

Sources & evidence

ORD record: ord-8994ba26ee3c4bde9c505e840d758149
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

Loading…