3-[2-(2-Nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone → N-(2-Bromoethyl)-2-nitro-1H-imidazole-1-ethanamine, monohydrobromide

HRID 1461105Notes

Reaction equation

HRID 1461105 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14]OC2=O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[BrH:17].C(O)(=O)C>CCOCC.CO>[BrH:17].[Br:17][CH2:14][CH2:15][NH:11][CH2:10][CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 148966263-[2-(2-Nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinoneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 14896628N-(2-Bromoethyl)-2-nitro-1H-imidazole-1-ethanamine, monohydrobromide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 3.5 g (15 mmol) of 3-[2-(2-nitro-1H-imidazol-1-yl)ethyl-2-oxazolidinone was added 30 ml of 31% HBr/acetic acid and the mixture was stirred for 18 hours at 20°-25° C. The mixture was diluted with ether and methanol and the resulting solid was collected. Recrystallization from ethanol/water gave 3.0 g of the desired product, N-(2-bromoethyl)-2-nitro-1H-imidazole-1-ethanamine, monohydrobromide (54%): mp 103°-104° C.

Workup

  1. customthe resulting solid was collected
  2. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-a260a1abc1ef4fc783c7e37367bcaf78
Source dataset
uspto-grants-1991_12
Patent number
US05073639

Reaction notes

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