2-Nitroimidazole → (S)-(+)-alpha-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol

HRID 266716Notes

Reaction equation

HRID 266716 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([C@H:17]1[O:19][CH2:18]1)[Cl:16]>>[Cl:16][CH2:15][C@@H:17]([OH:19])[CH2:18][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 149428(+)-Epichlorohydrin

Product 1

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

Procedure

Alternatively, a mixture of 2-nitroimidazole, anhydrous potassium carbonate, and (S)-(+)-epichlorohydrin is refluxed for 10 minutes then filtered while hot. The filtrate is concentrated and cooled to give a solid. Crystallization from ethanol and further processing gives the product.

Workup

  1. temperatureis refluxed for 10 minutes
  2. filtrationthen filtered while hot
  3. concentrationThe filtrate is concentrated
  4. temperaturecooled
  5. customto give a solid
  6. customCrystallization from ethanol and further processing
  7. customgives the product

Sources & evidence

ORD record
ord-8b9f44a2c47945cba8d44e8530187c1a
Source dataset
uspto-grants-1997_07
Patent number
US05652255

Reaction notes

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