2-Chloroacrylonitrile → HCID 13361511, compound

HRID 1788747Notes

Reaction equation

HRID 1788747 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[Hg]Cl)(=[O:3])[CH3:2].[Cl:13][C:14](=[CH2:17])[C:15]#[N:16].[BH4-].[Na+]>C(O)C>[C:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[CH2:17][CH:14]([Cl:13])[C:15]#[N:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 701982-ChloroacrylonitrileHCID 4311764Sodium borohydrideHCID 12257140HCID 12257140, compound

Product 1

HCID 13361511HCID 13361511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

31 g of trans-1-acetamido-2-chloromercuriocyclohexane are suspended in 250 ml of 95% strength ethanol: 187 ml (4 equivalents) of 2-chloroacrylonitrile are added. While cooling in ice, a solution of 3 g of sodium borohydride in 50 ml of ethanol is added as rapidly as possible. After warming up to room temperature, the precipitated elemental mercury is filtered off with suction over kieselguhr, thoroughly washed with ethanol and the filtrate is evaporated. The residue is taken up in methylene chloride, washed three times with 1N sodium hydroxide solution to destroy the boric esters, dried over sodium sulfate and evaporated. 13 g of the title compound are obtained as a yellow oil.

Workup

  1. temperatureWhile cooling in ice
  2. filtrationthe precipitated elemental mercury is filtered off with suction over kieselguhr
  3. washthoroughly washed with ethanol
  4. customthe filtrate is evaporated
  5. washwashed three times with 1N sodium hydroxide solution
  6. customto destroy the boric esters
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-9c1a67b4b67e42289524d20455c072ac
Source dataset
uspto-grants-1987_08
Patent number
US04684662

Reaction notes

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