Ethyl Acetate → HCID 18388859, compound

HRID 2296978Notes

Reaction equation

HRID 2296978 reaction equation
Cl[C:2]([Cl:12])(OC(=O)OC(Cl)(Cl)Cl)Cl.C[N:14](C)[NH:15][C:16]([NH:18][CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=1)[CH3:20])=[O:17].[C:34](OCC)(=O)C>C(Cl)Cl>[Cl:12][C:2]1[N:18]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:22]=2)[CH3:20])[C:16](=[O:17])[N:15]([CH3:34])[N:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 18388805HCID 18388805, compound

Product 1

HCID 18388859HCID 18388859, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.33 g (14.6 mmol) of triphosgene in 15 ml of methylene chloride was added dropwise a solution of 2.07 g (7.30 mmol) of 1,1-dimethyl-4-{1-(3-phenylphenyl)ethyl}semicarbazide (produced in the following Reference Production Example 7) in 20 ml of methylene chloride with ice-cooling. The mixture was removed from an ice bath, warmed to room temperature and heated under reflux for 4 hours. After allowing to cool to room temperature, the reaction mixture was poured into 150 ml of an about 5% aqueous solution of sodium bicarbonate, and the mixture was stirred for 1 hour. The organic layer was washed with water, dried and concentrated. The residue (1.93 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=10:1 and then 5:1 and then 3:1) to obtain 418 mg (1.33 mmol) of 5-chloro-2-methyl-4-{1-(3-phenylphenyl)ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound 12 of the present invention) as an oil.

Workup

  1. temperaturecooling
  2. customThe mixture was removed from an ice bath
  3. temperatureheated
  4. temperatureunder reflux for 4 hours
  5. temperatureto cool to room temperature
  6. additionthe reaction mixture was poured into 150 ml of an about 5% aqueous solution of sodium bicarbonate
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated
  10. washeluted with n-hexane

Sources & evidence

ORD record
ord-1ca801d90fc045ed9a3a9175a22eebbc
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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