Methyl iodide → 1-(2-Methoxy-1,1-dimethyl-ethyl)-4-nitro-1H-imidazole

HRID 553088Notes

Reaction equation

HRID 553088 reaction equation
[CH3:1][O:2][C:3](=O)[C:4]([CH3:14])([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[N:8]=[CH:7]1)[CH3:5].[BH4-].[Na+].CI.[H-].[Na+]>CO>[CH3:1][O:2][CH2:3][C:4]([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[N:8]=[CH:7]1)([CH3:14])[CH3:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 67164903methyl 2-methyl-2-(4-nitro-1H-imidazol-1-yl)propanoate

Product 1

HCID 671644331-(2-Methoxy-1,1-dimethyl-ethyl)-4-nitro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-2-(4-nitro-imidazol-1-yl)-propionic acid methyl ester was reduced using sodium borohydride in methanol and the resultant alcohol was alkylated with methyl iodide using sodium hydride as base to provide the title compound: H1 NMR (400 MHz, CDCl3) 1.53 (s, 6H), 3.25 (s, 3H), 3.38 (s, 2H), 7.53 (s, 1H), 7.88 (s, 1H).

Sources & evidence

ORD record
ord-fe74506628a045ec9ed2a89da8c179dd
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

Loading…