2-Chloroacrylonitrile → HCID 13361513, compound

HRID 1788749Notes

Reaction equation

HRID 1788749 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[Hg]Cl)(=[O:3])[CH3:2].[Cl:12][C:13](=[CH2:16])[C:14]#[N:15].[BH4-].[Na+]>C(O)C>[C:1]([NH:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[CH2:16][CH:13]([Cl:12])[C:14]#[N:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 701982-ChloroacrylonitrileHCID 4311764Sodium borohydrideHCID 12257138HCID 12257138, compound

Product 1

HCID 13361513HCID 13361513, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

16.1 g of trans-1-acetamido-2-chloromercuriocyclopentane are suspended in 200 ml of ethanol. 10.7 ml of 2-chloroacrylonitrile are added, followed by 1.7 g of sodium borohydride in 40 ml of ethanol as rapidly as possible while cooling in ice. After 1 hour at room temperature, the mixture is filtered with suction through kieselguhr, the filtrate is evaporated, the residue is taken up with methylene chloride, this solution is washed twice with 1N sodium hydroxide solution, and the organic phase is dried over sodium sulfate and evaporated. Chromatography on silica gel (mobile phase ethyl acetate) produces 2.2 g of crystalline product, melting point 114°-117° C.

Workup

  1. temperaturewhile cooling in ice
  2. filtrationthe mixture is filtered with suction through kieselguhr
  3. customthe filtrate is evaporated
  4. washthis solution is washed twice with 1N sodium hydroxide solution
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d90b8545ce624e38851dac4a9f3f4f7e
Source dataset
uspto-grants-1987_08
Patent number
US04684662

Reaction notes

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