Ethyl Acetate → 5-chloro-2-methyl-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 2296997Notes

Reaction equation

HRID 2296997 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]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:22][C:21]=1[CH3:32])=[O:17].[C:34](OCC)(=O)C>C(Cl)Cl>[Cl:12][C:2]1[N:18]([CH2:19][C:20]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][C:21]=2[CH3:32])[C:16](=[O:17])[N:15]([CH3:34])[N:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 183888861,1-Dimethyl-4-(2-methyl-5-phenylbenzyl)semicarbazide

Product 1

HCID 120565155-chloro-2-methyl-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9.24 g (31.1 mmol) of triphosgene in 50 ml of methylene chloride was added dropwise a solution of 4.41 g (15.6 mmol) of 1,1-dimethyl-4-(2-methyl-5-phenylbenzyl)semicarbazide (produced in the following Reference Production Example 15) in 35 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 6 hours. After allowing to cool to room temperature, the reaction mixture was poured into 300 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 was subjected to silica gel column chromatography (developed with n-hexane:ethyl acetate=2:1and then 1:1) to obtain 2.01 g (6.4 mmol) of 5-chloro-2-methyl-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound 7 of the present invention) having a melting point of 115.7° C.

Workup

  1. temperaturecooling
  2. customThe mixture was removed from an ice bath
  3. temperatureheated
  4. temperatureunder reflux for 6 hours
  5. temperatureto cool to room temperature
  6. additionthe reaction mixture was poured into 300 ml of an about 5% aqueous solution of sodium bicarbonate
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3283343d4ef34d2aace9518adf9acad0
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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