Tetrahydrofuran → HCID 13208971, compound

HRID 1248632Notes

Reaction equation

HRID 1248632 reaction equation
[N+:1]([CH:4]=[C:5]([S:10][CH3:11])[NH:6][CH2:7][CH2:8]Br)([O-:3])=[O:2].O1CCCC1>>[CH3:11][S:10][C:5]1[NH:6][CH2:7][CH2:8][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 85445244HCID 85445244, compound

Product 1

HCID 13208971HCID 13208971, compoundYield 26%

Procedure

(ii) A solution of 1-nitro-2-methylthio-2-(2-bromoethylamino) ethylene (3g, 0.012 mol) and solium hydride (50% in oil, 0.62 g, 0.013 mol) in dry tetrahydrofuran (100 mol) was refluxed for 7 hours. The reaction mixture was cooled, and the solvent was removed in vacuo. The residue was extracted with boiling ethyl acetate (2×50 ml), and the extracts were decolourized with charcoal. Concentration of the extracts in vacuo, followed by cooling, resulted in the crystallisation of 2-methylthio-3-nitro-4,5-dihydropyrrole (0.5 g, 26%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was removed in vacuo
  3. extractionThe residue was extracted with boiling ethyl acetate (2×50 ml)
  4. temperatureby cooling

Sources & evidence

ORD record
ord-526e9adacc914782a6b972d7cfd38afd
Source dataset
uspto-grants-1985_06
Patent number
US04525477

Reaction notes

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