Carbon Tetrachloride → HCID 14877940, compound

HRID 1460328Notes

Reaction equation

HRID 1460328 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([NH:15][C:16](=O)[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[N-:50]=[N+:51]=[N-:52].[Na+]>C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([N:15]2[C:16]([CH3:17])=[N:52][N:51]=[N:50]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 14877938HCID 14877938, compound

Product 1

HCID 14877940HCID 14877940, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5.54 g (16.1 mmoles) of ethyl 3,3-bis(4-fluorophenyl)-2-(acetylamino)-2-propenoate and 9.3 g of triphenylphosphine in 120 mL of dry acetonitrile at room temperature was added dropwise 6.82 mL of carbon tetrachloride. The pale suspension was stirred for 45 minutes. To this clear orange solution was added 2.3 g of sodium azide and 0.6 g of tetra n-butyl ammonium bromide and stirring was continued. The orange suspension soon became pale with the formation of a white precipitate. After 3 hours, the mixture was filtered and the solution was concentrated under reduced pressure. More triphenylphosphine oxide was removed and the desired product was purified by crystallizations from ethyl acetate-hexanes to give 5.3 g (88%) of the title compound; m.p.=102.9°-103.5° C.

Workup

  1. stirringstirring
  2. waitAfter 3 hours
  3. filtrationthe mixture was filtered
  4. concentrationthe solution was concentrated under reduced pressure
  5. customMore triphenylphosphine oxide was removed
  6. customthe desired product was purified by crystallizations from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-a916cc0c037c40299bd06c2ec9775bbe
Source dataset
uspto-grants-1991_12
Patent number
US05070206

Reaction notes

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