Oxygen → Ipronidazole-hydroxy

HRID 441709Notes

Reaction equation

HRID 441709 reaction equation
C([O:3]P(OCC)OCC)C.[OH-].[K+].[CH3:13][N:14]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=[C:15]1[CH:22]([CH3:24])[CH3:23].O=O>O=P(N(C)C)(N(C)C)N(C)C.O.C(O)(=O)C>[OH:3][C:22]([C:15]1[N:14]([CH3:13])[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=1)([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 977OxygenHCID 14797Potassium HydroxideHCID 26951IpronidazoleHCID 31215Triethyl phosphite

Product 1

HCID 598402Ipronidazole-hydroxyYield 21.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A total of 11.2 ml of triethylphosphite and 6 g of powdered potassium hydroxide were added to a solution of 8.5 g of 1-methyl-2-isopropyl-5-nitroimidazole in 40 ml of hexametapol while cooling in an ice-bath. While the solution was further cooled with ice, oxygen was conducted through the solution with vigorous stirring. After 2.5 hours, 6.1 ml of glacial acetic acid were added and the mixture was then poured into 600 ml of water and extracted four times with 150 ml portions of ether. The ether extracts were washed with a small amount of water, evaporated on a rotary evaporator and finally dried at 85°/0.5 Torr. The residue was crystallized from 15 ml of isopropyl ether. There were obtained 2.0 g of 2-(2-hydroxy-2-propyl)-1-methyl-5-nitroimidazole, melting point 102°-107°. The yield was 21.6%.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. extractionextracted four times with 150 ml portions of ether
  3. washThe ether extracts were washed with a small amount of water
  4. customevaporated on a rotary evaporator
  5. customfinally dried at 85°/0.5 Torr
  6. customThe residue was crystallized from 15 ml of isopropyl ether

Sources & evidence

ORD record
ord-fb3ffaff86e7458089a3b4ce9a58ed2f
Source dataset
uspto-grants-1977_08
Patent number
US04042597

Reaction notes

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