Dichloromethane → HCID 73433315, compound

HRID 2296966Notes

Reaction equation

HRID 2296966 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](=[N:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27])[CH:21]=1)=[O:17].[CH2:38](Cl)Cl>>[Cl:12][C:2]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=[N:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:27])[CH:21]=2)[C:16](=[O:17])[N:15]([CH3:38])[N:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 94429TriphosgeneHCID 73433314HCID 73433314, compound

Product 1

HCID 73433315HCID 73433315, compound

Procedure

To a solution of 0.96 g (3.24 mmol) of triphosgene in 10 ml of dry methylene chloride was added dropwise a solution of 0.55 g (1.62 mmol) of 1,1-dimethyl-4-{3-(1-(benzyloxyimino)ethyl)benzyl}semicarbazide (produced in the following Reference Production Example 2) in 15 ml of dry methylene dhloride with ice-cooling. The mixture was removed from an ice bath, then 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 40 ml of an about 5% aqueous solution of sodium bicarbonate, and the mixture was stirred for 0.5 hours. The organic layer was washed with water, dried and concentrated. The residue was subjected to silica gel preparative thin layer chromatography (developed with n-hexane:ethyl acetate=3:2) to obtain 0.27 g (0.74 mmol) of 5-chloro-2-methyl-4-{3-(1-(benzyloxyimino)ethyl)-benzyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound 249 of the present invention).

Workup

  1. customproduced in the following Reference Production Example 2) in 15 ml of dry methylene
  2. temperaturecooling
  3. customThe mixture was removed from an ice bath
  4. temperatureheated
  5. temperatureunder reflux for 4 hours
  6. temperatureto cool to room temperature
  7. additionthe reaction mixture was poured into 40 ml of an about 5% aqueous solution of sodium bicarbonate
  8. washThe organic layer was washed with water
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ea1b643112464d2eb441d53627506dc7
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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