Carbon Tetrachloride → HCID 14877939, compound

HRID 1460323Notes

Reaction equation

HRID 1460323 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:9]([NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[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-:55]=[N+:56]=[N-:57].[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:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:9]([N:15]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:57][N:56]=[N:55]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 14877937HCID 14877937, compound

Product 1

HCID 14877939HCID 14877939, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5.8 g (14 mmoles) of ethyl 3,3-bis(4-fluorophenyl)-2-(benzoylamino)-2-propenoate and 11.2 g of triphenylphosphine in 150 mL of dry acetonitrile at room temperature was added dropwise 8.3 mL of carbon tetrachloride. The pale suspension was stirred for 45 minutes. To this clear orange solution was added 2.8 g of sodium azide and 1 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 three 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 4.2 g (69%) of the title compound; m.p.=148.6°-150.1° C.

Workup

  1. stirringstirring
  2. waitAfter three 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-150ee7f7b1d048f9be0a3376bd946f43
Source dataset
uspto-grants-1991_12
Patent number
US05070206

Reaction notes

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