Water → HCID 53735293, compound

HRID 1262866Notes

Reaction equation

HRID 1262866 reaction equation
[C:1]([CH:3]1[CH2:11][CH:10]2[CH:5]3[CH2:6][CH:7]4[CH:9]2[CH:8]4[CH:4]13)#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:13].O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1([Cl:13])[CH2:11][CH:10]2[CH:5]3[CH2:6][CH:7]4[CH:9]2[CH:8]4[CH:4]13)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 12463755HCID 12463755, compound

Product 1

HCID 53735293HCID 53735293, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 8-cyanotetracyclo-[4,3,0,02,4,03,7 ]nonane (87 g.) in carbon tetrachloride (600 ml.) was added phosphorus pentachloride (168 g.). The mixture was heated under reflux for 60 hours, cooled and poured into a mixture of crushed ice and water (1.1). The mixture was stirred for 30 minutes and the organic layer separated. This was washed with a 10% w/v aqueous solution of sodium carbonate (200 ml.), saturated brine (100 ml.) and then dried over anhydrous potassium carbonate. The filtrate was then evaporated in vacuo to remove solvent and then distilled in vacuo to give 8-cyano-8-chlorotetracyclo[4,3,0,02,4,03,7 ]nonane, b.p. 136°-140° C./20 mm., in 83% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 60 hours
  3. temperaturecooled
  4. customthe organic layer separated
  5. washThis was washed with a 10% w/v aqueous solution of sodium carbonate (200 ml.), saturated brine (100 ml.)
  6. dry with materialdried over anhydrous potassium carbonate
  7. customThe filtrate was then evaporated in vacuo
  8. customto remove solvent
  9. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-9459a04d457841c0b46e987a428944d7
Source dataset
uspto-grants-1984_06
Patent number
US04454157

Reaction notes

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