Hydrochloric Acid → HCID 15022937, compound

HRID 1587242Notes

Reaction equation

HRID 1587242 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:32])=[CH:17][C:18]([Cl:31])=[C:19]([N:21]2[C:25](=[O:26])[N:24]([CH:27]([F:29])[F:28])[C:23]([CH3:30])=[N:22]2)[CH:20]=1.[ClH:33]>C(#N)C.[Cu](Cl)Cl>[Cl:33][CH:2]([CH2:3][C:15]1[CH:20]=[C:19]([N:21]2[C:25](=[O:26])[N:24]([CH:27]([F:29])[F:28])[C:23]([CH3:30])=[N:22]2)[C:18]([Cl:31])=[CH:17][C:16]=1[Cl:32])[C:1]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 10906Tert-Butyl nitriteHCID 110559662-(5-Amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one

Product 1

HCID 15022937HCID 15022937, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.), stirred mixture of 28.7 g (0.333 mole) of methyl acrylate, 2.51 g (0.0244 mole) of tertbutyl nitrite, and 2.6 g (0.019 mole) of copper (II) chloride in 50 mL of acetonitrile was added dropwise a solution of 5.0 g (0.016 mole) of 1-(5-amino-2,4-dichlorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 15 mL of acetonitrile. After complete addition the reaction mixture was allowed to warm to room temperature and was stirred for approximately 18 hours. The reaction mixture was diluted with 15 mL of 2N hydrochloric acid solution. The mixture was extracted with four portions of diethyl ether. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to give an oil. The oil was purified by column chromatography on silica gel, eluting with n-heptane:ethyl acetate (4:1) to give 5.0 g of methyl 2-chloro-3-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionate as an oil, Compound 3 of Table 1.

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperatureto warm to room temperature
  3. stirringwas stirred for approximately 18 hours
  4. extractionThe mixture was extracted with four portions of diethyl ether
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customto give an oil
  9. customThe oil was purified by column chromatography on silica gel
  10. washeluting with n-heptane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-059f773113a747a9a3b3287f903d39f8
Source dataset
uspto-grants-1993_06
Patent number
US05217520

Reaction notes

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