Sodium hydride → HCID 12831745, compound

HRID 1995585Notes

Reaction equation

HRID 1995585 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 chromatographed 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°. Found: C, 41.5; H, 5.7; N, 16.1; S, 18.25; C6H10N2O2S requires: C, 41.4; H, 5.8; N, 16.1; S, 18.4%.

Workup

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

Sources & evidence

ORD record
ord-a0c51f7f50b94749b8da0d6119f7ca3a
Source dataset
uspto-grants-1983_09
Patent number
US04405624

Reaction notes

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