Ethyl Acetate → HCID 15510049, compound

HRID 2296961Notes

Reaction equation

HRID 2296961 reaction equation
Cl[C:2]([Cl:12])(OC(=O)OC(Cl)(Cl)Cl)Cl.C[N:14](C)[NH:15][C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=1)=[O:17].[C:33](OCC)(=O)C>C(Cl)Cl>[Cl:12][C:2]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:21]=2)[C:16](=[O:17])[N:15]([CH3:33])[N:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 18388843HCID 18388843, compound

Product 1

HCID 15510049HCID 15510049, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.75 g (9.28 mmol) of triphosgene in 15 ml of methylene chloride was added dropwise a solution of 1.25 g (4.64 mmol) of 1,1-dimethyl-4-(3-phenylbenzyl)semicarbazide (produced in the following Reference Production Example 1) in 10 ml of methylene chloride with ice-cooling. The mixture was removed from an ice bath, allowed to warm to room temperature, and heated under reflux for 4 hours. After allowing to cool to room temperature, the reaction mixture was poured into 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 was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=5:1 and then 3:1) to obtain 0.59 g (2.0 mmol) of 5-chloro-2-methyl-4-(3-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound 2 of the present invention).

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 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-55c586b11ec240d092c660c822c79a69
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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