Sodium Hydroxide → (S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole

HRID 2258142Notes

Reaction equation

HRID 2258142 reaction equation
Cl[CH2:2][C@@H:3]([OH:13])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[N+:10]([O-:12])=[O:11].[OH-].[Na+]>>[N+:10]([C:6]1[N:5]([CH2:4][C@H:3]2[CH2:2][O:13]2)[CH:9]=[CH:8][N:7]=1)([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 11052772(S)-(+)-alpha-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol

Product 1

HCID 11768967(S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazoleYield 65.1%

Procedure

Alternatively, reaction of 0.56 g of (S)-(+)-α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol with 3 mL of 10% aqueous sodium hydroxide at 25° C. for 30 minutes followed by further processing as above gives 0.3 g of the product.

Sources & evidence

ORD record
ord-9d60399850bf469d9fdc5544c0c7eee7
Source dataset
uspto-grants-1997_08
Patent number
US05659048

Reaction notes

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