2-Methyl-2-butene → 5-methyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid

Reaction equation

[CH3:1][C:2]1[NH:6][C:5]([CH:7]=[O:8])=[N:4][C:3]=1[C:9]([F:12])([F:11])[F:10].Cl([O-])=[O:14].[Na+].P([O-])(O)(O)=O.[Na+].CC(=CC)C>>[CH3:1][C:2]1[NH:6][C:5]([C:7]([OH:14])=[O:8])=[N:4][C:3]=1[C:9]([F:12])([F:10])[F:11]

Participants

Reactant 4

HCID 105532-Methyl-2-butene

HCID 23668197Sodium Chlorite

HCID 23672064Monosodium phosphate

HCID 866484815-Methyl-4-(trifluoromethyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 675498085-methyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acidYield 118.2%

Procedure

The same operation as in Example (33c) was performed using 5-methyl-4-(trifluoromethyl)-1H-imidazole-2-carbaldehyde obtained in Example (36c) (90 mg, 0.51 mmol), sodium chlorite (95 mg, 1.05 mmol), sodium dihydrogenphosphate (154 mg, 0.99 mmol) and 2-methyl-2-butene (0.3 mL, 2.84 mmol), to obtain 117 mg of the title compound as a white solid (100%).

Sources & evidence

ORD record: ord-3d5e398ed2a04ef081f57c6cbf8e141e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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