Pyridine → 1-Nitroso-4-(2-thenoyl)piperazine

HRID 1655192Notes

Reaction equation

HRID 1655192 reaction equation
[N:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=[O:2].N1C=CC=CC=1.[C:15]1([C:20](Cl)=[O:21])[S:19][CH:18]=[CH:17][CH:16]=1.C(OCC)(=O)C>O1CCOCC1.O>[N:1]([N:3]1[CH2:8][CH2:7][N:6]([C:20](=[O:21])[C:15]2[S:19][CH:18]=[CH:17][CH:16]=2)[CH2:5][CH2:4]1)=[O:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 21845N-NitrosopiperazineHCID 789282-Thiophenecarbonyl chloride

Product 1

HCID 197912611-Nitroso-4-(2-thenoyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1-nitrosopiperazine {1.21 g) and pyridine (2.4 ml) in dioxane (18 ml) was added dropwise 2-thenoyl chloride (1.2 ml) in an ice bath. The mixture was stirred for one hour in an ice.bath and then overnight at ambient temperature. The mixture was poured into a mixture of ethyl acetate (100 ml) and water (100 ml). The separated aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. The residue was pulverized with diisopropyl ether to yield 1-nitroso-4-(2-thenoyl)-piperazine (1.78 g).

Workup

  1. customovernight
  2. customat ambient temperature
  3. extractionThe separated aqueous layer was extracted twice with ethyl acetate
  4. customThe combined organic layers were dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfc195a29747483781bbdce8c9fc94ce
Source dataset
uspto-grants-1993_10
Patent number
US05250528

Reaction notes

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