Hydrochloric Acid → HCID 9927979, compound

HRID 396420Notes

Reaction equation

HRID 396420 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([N+:15]#[C-:16])[CH:3]=1.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][C:6]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:14][CH:13]=2)[NH:15][C:16]=1[C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 7412Benzoyl chlorideHCID 23003593HCID 23003593, compound

Product 1

HCID 9927979HCID 9927979, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl trans-4-chloro-2-isocyanocinnamate (step 4, 1.2 g, 5.1 mmol), tributyltin hydride (1.6 g, 5.6 mmol) and AIBN (43 mg, 0.26 mmol) in acetonitrile (30 ml) was heated at 100° C. After 1 h, tetrakis(triphenylphosphine)palladium (580 mg, 0.50 mmol) and benzoyl chloride (0.65 ml, 5.6 mmol) were added and the mixture was heated for a further 17 h. The mixture was cooled and poured into 2N aqueous HCl (50 ml) and extracted with diethyl ether (80 ml×2). The combined organic extracts were washed with saturated aqueous potassium fluoride (50 ml) and dried (MgSO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with ethyl acetate/hexane (1:5) to afford 0.43 g (25%) of the title compound as white solids.

Workup

  1. temperaturethe mixture was heated for a further 17 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether (80 ml×2)
  4. washThe combined organic extracts were washed with saturated aqueous potassium fluoride (50 ml)
  5. dry with materialdried (MgSO4)
  6. customAfter removal of solvent
  7. customthe crude product was purified by flash column chromatography
  8. washeluting with ethyl acetate/hexane (1:5)

Sources & evidence

ORD record
ord-1569666efe0642e49dba5f85c6a7fd68
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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