Hydrochloric Acid → HCID 15477192, compound

HRID 840354Notes

Reaction equation

HRID 840354 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].N(OC(C)(C)C)=O.N[C:15]1[C:16]([Cl:33])=[CH:17][C:18]([F:32])=[C:19]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[CH:20]=1.[ClH:34]>C(#N)C.[Cu](Cl)Cl>[Cl:34][CH:2]([CH2:3][C:15]1[CH:20]=[C:19]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[C:18]([F:32])=[CH:17][C:16]=1[Cl:33])[C:1]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 10906Tert-Butyl nitriteHCID 11449172HCID 11449172, compound

Product 1

HCID 15477192HCID 15477192, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

In 20 ml of acetonitrile were dissolved 3.44 g of methyl acrylate and 0.62 g of t-butyl nitrite, and 0.65 g of copper (II) chloride was added. Under stirring, 1.16 g of N-(5-amino-4-chloro-2-fluorophenyl)phthalimide was added thereto in small portions, followed by stirring at room temperature for 1 hour. 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=1:5) to give 0.98 g of the title compound (No. 4 of Table 1).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 1 hour
  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=1:5)

Sources & evidence

ORD record
ord-310fc01372784df99d69f18c9a292256
Source dataset
uspto-grants-2002_04
Patent number
US06365753B1

Reaction notes

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