Sodium hydride → HCID 12831745, compound

HRID 1248629Notes

Reaction equation

HRID 1248629 reaction equation
[N+:1]([CH:4]=[C:5]([S:11][CH3:12])[NH:6][CH2:7][CH2:8][CH2:9]Br)([O-:3])=[O:2].[H-].[Na+]>O1CCCC1>[CH3:12][S:11][C:5]1[NH:6][CH2:7][CH2:8][CH2:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 85445243HCID 85445243, compound

Product 1

HCID 12831745HCID 12831745, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-nitro-2-methylthio-2-(3-bromopropylamino)ethylene (3.2 g, 0.012 mol) and sodium hydride (50% in oil, 0.9 g, 0.019 mol) in dry tetrahydrofuran (50 ml) was refluxed for 18 hours. The mixture was filtered, and the filtrate was evaporated to dryness. The residue was chromatograped on a silica gel column, the product being eluted with ethyl acetate. Recrystallisation of the product from methanol/propan-2-ol gave 2-methylthio-3-nitro-1,4,5,6-tetrahydropyridine (0.6 g, 29%) m.p. 230.5°-231.5°.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. washthe product being eluted with ethyl acetate
  5. customRecrystallisation of the product from methanol/propan-2-ol

Sources & evidence

ORD record
ord-b59d1824845e4e619ef5cc17a3ef22dc
Source dataset
uspto-grants-1985_06
Patent number
US04525477

Reaction notes

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