Diethyl Ether → HCID 178486115, compound

HRID 1578997Notes

Reaction equation

HRID 1578997 reaction equation
[Cl-].[CH3:2][N:3]([S+:5]([N:9]([CH3:11])[CH3:10])[N:6]([CH3:8])[CH3:7])[CH3:4].[O-:12][C:13]#[N:14].[Na+].CCOCC>CO>[O-:12][C:13]#[N:14].[CH3:2][N:3]([S+:5]([N:9]([CH3:11])[CH3:10])[N:6]([CH3:8])[CH3:7])[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 517096Sodium CyanateHCID 86733077HCID 86733077, compound

Product 1

HCID 178486115HCID 178486115, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 10 g (0.05 mole) of tris(dimethylamino)sulfonium chloride and 3.6 g (0.055 mole) powdered sodium cyanate in 100 ml methanol was stirred at room temperature (25°) for 3 days. Ether, 300 ml, was added, and the precipitated sodium chloride was filtered off. The filtrate was evaporated to dryness under reduced pressure and the residue was redissolved in acetonitrile, filtered, and then precipitated by the addition of ether. The precipitate was collected on a filter, washed with ether, and dried under dry nitrogen to give 9.27 g (90%) of tris(dimethylamino)sulfonium cyanate as a white crystalline powder, m.p. 202°-204°.

Workup

  1. filtrationthe precipitated sodium chloride was filtered off
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionthe residue was redissolved in acetonitrile
  4. filtrationfiltered
  5. customprecipitated by the addition of ether
  6. customThe precipitate was collected on a filter
  7. washwashed with ether
  8. customdried under dry nitrogen

Sources & evidence

ORD record
ord-7cee66f468644d9985726c8e44ebeb95
Source dataset
uspto-grants-1976_02
Patent number
US03940402

Reaction notes

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