4-Hexen-3-one, 5-hydroxy-, (Z)-(9CI) → HCID 178426634, compound

HRID 450855Notes

Reaction equation

HRID 450855 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[S:5])#[N:2].[Na].C([C:10](O)=[CH:11][C:12](=O)[CH3:13])C.[C:16](O)(=O)C.N1CCCCC1>O.C(O)(=O)C>[CH3:13][C:12]1[C:11]([CH3:10])=[N:6][C:4]([SH:5])=[C:3]([CH:16]=1)[C:1]#[N:2]

Participants

7

Reactant 4

HCID 5173964-Hexen-3-one, 5-hydroxy-, (Z)-(9CI)HCID 14162772-CyanoethanethioamideHCID 5360545SodiumHCID 9793820Piperidine, acetate

Product 1

HCID 178426634HCID 178426634, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of cyanothioacetamide (2.0 g, 20 mmol), the sodium salt of ethyl-3-oxo-butenol (2.44 g, 20 mmol) and piperidine acetate (1.9 ml) in water (20 ml) is heated at reflux before adding acetic acid (3 ml). The resulting precipitate is filtered and washed with water. The crude product is dissolved by heating in methanol. Filtering and evaporation of the solvent under reduced pressure yields 5,6-dimethyl-2-mercapto-nicotine nitrile.

Workup

  1. temperatureat reflux
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water
  4. dissolutionThe crude product is dissolved
  5. temperatureby heating in methanol
  6. filtrationFiltering
  7. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ebca332f752449f9a402fabb528f51a7
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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