Carbon Tetrachloride → HCID 70317767, compound

HRID 2181277Notes

Reaction equation

HRID 2181277 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[F:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[C:33]1([S:47]([C:50]2[CH:55]=[CH:54][C:53]([CH:56]=O)=[CH:52][CH:51]=2)(=[O:49])=[O:48])[CH2:38][CH2:37][CH:36]([NH:39][S:40]([C:43]([F:46])([F:45])[F:44])(=[O:42])=[O:41])[CH2:35][CH2:34]1.C(#[N:60])C>O>[C:56]([C:53]1[CH:54]=[CH:55][C:50]([S:47]([C:33]2([C:27]3[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=3[F:25])[CH2:38][CH2:37][CH:36]([NH:39][S:40]([C:43]([F:46])([F:45])[F:44])(=[O:42])=[O:41])[CH2:35][CH2:34]2)(=[O:49])=[O:48])=[CH:51][CH:52]=1)#[N:60]

Participants

6

Reactant 4

HCID 5943Carbon Tetrachloride2×HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 20781254HCID 20781254, compound

Product 1

HCID 70317767HCID 70317767, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenyl phosphine (0.32 g, 1.2 mmol), followed by carbon tetrachloride (0.06 ml, 0.60 mmol), were added to a solution of the product from Example 80 (0.16 g, 0.30 mmol) in acetonitrile (1.5 ml). The mixture was stirred for 1.5 hours, additional carbon tetrachloride (0.18 ml, 0.18 mmol) was added, and the mixture was stirred for 0.5 hours, diluted with water (10 ml) and extracted with diethyl ether (2×10 ml). The combined organic phases were washed with brine (sat. 20 ml), dried (magnesium sulfate) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with 20% ethyl acetate/isohexane to give the nitrile (0.11 g, 71%). 1H NMR (CDCl3, 360 MHz): 1.63-1.69 (2H, m), 2.04-2.09 (2H, m), 2.48 (2H, bt, J=13.0), 2.59-2.64 (2H, m), 3.81 (1H, m), 5.66 (1H, d, J=7.3), 6.79-6.86 (1H, m), 7.07-7.13 (2H, m), 7.52 (2H, d, J=8.5), 7.70 (2H, d, J=8.5)

Workup

  1. stirringthe mixture was stirred for 0.5 hours
  2. extractionextracted with diethyl ether (2×10 ml)
  3. washThe combined organic phases were washed with brine (sat. 20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated in vacuo
  6. customThe crude product was chromatographed on silica
  7. washeluting with 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-99c8413c8b30447eae626c28fcfebc18
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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