2-Nitroimidazole → HCID 178437198, compound

HRID 893973Notes

Reaction equation

HRID 893973 reaction equation
[Na].[N+:2]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)([O-:4])=[O:3].Cl.Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C[O-].[Na+]>C1(C)C(C)=CC=CC=1>[N:14]1([CH:13]([C:7]2[N:6]=[C:5]([N+:2]([O-:4])=[O:3])[NH:9][CH:8]=2)[CH3:12])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 107012-NitroimidazoleHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 178437198HCID 178437198, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

The sodium salt of 2-nitroimidazole (0.01 mole) was reacted with a mixture of 0.01 mole of N-(2-chloroethyl)piperidine hydrochloride and 0.01 mole of sodium methoxide in 20 ml of xylene. The mixture was heated at 140° C. under reflux for 8 hours. The mixture was filtered, the filtrate was concentrated under vacuum. The residue was crystallized from a mixture of ethyl ether and hexane to yield 0.007 mole of 1-piperidinoethyl-2-nitroimidazole, m.p. 61°-62° C. The 1-piperidinoethyl-2-nitroimidazole (0.01 mole) was treated with 0.01 mole of m-chloroperbenzoic acid (m--CPBA) at room temperature for 30 minutes in 100 ml of chloroform as solvent. The resulting N-oxide was purified by recrystallization from chloroform and benzene, and had a m.p. of 108°-109° C. 'H-nmr: (CD3OD) 7.12 and 7.47 (S, C4,5 -H), ##STR16## 3.60 (t, NCH2) ppm.ir: (KBr) 1485 and 1360 (NO2), 1270 cm-1 (N→O).

Workup

  1. temperatureunder reflux for 8 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was crystallized from a mixture of ethyl ether and hexane

Sources & evidence

ORD record
ord-93735dd6db3247c39d07a22c55737ecd
Source dataset
uspto-grants-1981_08
Patent number
US04282232

Reaction notes

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