Malononitrile → HCID 85985384, compound

HRID 2254515Notes

Reaction equation

HRID 2254515 reaction equation
[C:1]1([P:7]2(=[O:26])[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][C:10](=O)[CH:9]=[C:8]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27](#[N:31])[CH2:28][C:29]#[N:30]>C(O)C.N1CCCCC1>[C:29]([C:28]([C:27]#[N:31])=[C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[P:7](=[O:26])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9]1)#[N:30]

Participants

5

Reactant 2

HCID 8010MalononitrileHCID 12665063HCID 12665063, compound

Product 1

HCID 85985384HCID 85985384, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 0.25 g of 1,2,6-triphenylphospha-2,5-cyclohexadien-4-one P-oxide and 0.060 g of malononitrile in 100 ml of ethanol was added 1 drop of piperidine. The red mixture was heated on a steam bath for about one hour, then allowed to cool to room temperature overnight. The product crystallized as dark greenish brown metallic needles. It was collected and dried to give 0.247 g of 4-dicyanomethylene-1,2,6-triphenylphospha-2,5-cyclohexadiene P-oxide, whose structure was confirmed by 1HNMR and FDMS analyses.

Workup

  1. temperatureThe red mixture was heated on a steam bath for about one hour
  2. customThe product crystallized as dark greenish brown metallic needles
  3. customIt was collected
  4. customdried

Sources & evidence

ORD record
ord-bdbc4c66ef51468ca86d218a8778fb2b
Source dataset
uspto-grants-1993_08
Patent number
US05236797

Reaction notes

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