Hydrogen Bromide → 1H-Imidazole-1-ethanol, alpha-(((2-bromoethyl)amino)methyl)-2-nitro-, monohydrobromide, (R)-

HRID 2258143Notes

Reaction equation

HRID 2258143 reaction equation
[N:1]1([CH2:4][C@@H:5]([OH:15])[CH2:6][N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[N+:12]([O-:14])=[O:13])[CH2:3][CH2:2]1.[BrH:16]>CC(C)=O>[BrH:16].[Br:16][CH2:3][CH2:2][NH:1][CH2:4][C@@H:5]([OH:15])[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 10242276(R)-(-)-alpha-(1-Aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol

Product 1

HCID 1987901H-Imidazole-1-ethanol, alpha-(((2-bromoethyl)amino)methyl)-2-nitro-, monohydrobromide, (R)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In another alternate procedure, treatment of (R)-(-)-α-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol, synthesized as described in Example 2(e), with aqueous hydrogen bromide in acetone, as described in The Journal of Medicinal Chemistry, 33, 2608 (1990), gives the product, mp 149°-150.5° C. (decomposition), 99.3% optically pure by chiral HPLC.

Workup

  1. customgives the product, mp 149°-150.5° C. (decomposition), 99.3% optically pure by chiral HPLC

Sources & evidence

ORD record
ord-a242598137004891b4ddcd8bec42a73a
Source dataset
uspto-grants-1997_08
Patent number
US05659048

Reaction notes

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