Hydrochloric Acid → HCID 15477191, compound

HRID 840355Notes

Reaction equation

HRID 840355 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].N(OC(C)(C)C)=O.N[C:14]1[C:15]([Cl:32])=[CH:16][C:17]([F:31])=[C:18]([N:20]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])[CH:19]=1.[ClH:33]>C(#N)C.[Cu](Cl)Cl>[Cl:33][CH:2]([CH2:3][C:14]1[CH:19]=[C:18]([N:20]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])[C:17]([F:31])=[CH:16][C:15]=1[Cl:32])[C:1]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 10906Tert-Butyl nitriteHCID 11449172HCID 11449172, compound

Product 1

HCID 15477191HCID 15477191, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

In 200 ml of acetonitrile were dissolved 36.0 g of acrylic acid and 7.73 g of t-butyl nitrite, and 8.07 g of copper (II) chloride was added. Under stirring, 14.5 g of N-(5-amino-4-chloro-2-fluorophenyl)phthalimide was added thereto in small portions, followed by stirring at room temperature for 1.5 hours. 3N Hydrochloric acid was added to the reaction mixture. After stirring, the reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:1) to give 14.0 g of the title compound (No. 3 of Table 1).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 1.5 hours
  3. stirringAfter stirring
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-hexane=2:1)

Sources & evidence

ORD record
ord-a6c06a7e685f49c7aa5473c84c468897
Source dataset
uspto-grants-2002_04
Patent number
US06365753B1

Reaction notes

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