1-Methylimidazole → N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chloride

HRID 354211Notes

Reaction equation

HRID 354211 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:16])[CH2:11][O:12][C:13]([Cl:15])=[O:14])([O-:3])=[O:2].[CH3:17][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>ClCCl>[Cl-:15].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:16])[CH2:11][O:12][C:13]([N:20]1[CH:21]=[CH:22][N+:18]([CH3:17])=[CH:19]1)=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 114479052-(2-Nitrophenyl)propyl chloroformate

Product 1

HCID 11232610N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.07 ml 2-(2-nitrophenyl)propoxycarbonyl chloride (1) (4.4 mmol) are slowly added dropwise to a solution of 1.24 ml N-methylimidazole (14.7 mmol) in 40 ml dichloromethane at 0° C. over molecular sieve 4 Å. Following stirring for 30 minutes in an ice bath this solution is used directly for acylation with 1.2 equivalents of the 5′-O-protected nucleoside building blocks.

Sources & evidence

ORD record
ord-1487ffc257de4f5f9cb5e2ac9376ae8f
Source dataset
uspto-grants-2004_06
Patent number
US06756492B1

Reaction notes

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