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Hydrochloric Acid → N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-nitrobenzamide

HRID 848956
Notes
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Reaction equation

HRID 848956 reaction equation
[CH2:1]([NH:4][C:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:12]=2[Cl:19])[N:6]=1)[CH2:2][CH3:3].[N+:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([O-:22])=[O:21].Cl.[OH-].[Na+]>O1CCCC1.N1C=CC=CC=1.O>[O:10]=[C:8]1[N:7]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][C:12]=2[Cl:19])[N:6]=[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8495Benzoyl chloride, 3-nitro-2×HCID 14798Sodium HydroxideHCID 178456949HCID 178456949, compound

Product 1

HCID 19369062N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-nitrobenzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 1049PyridineSolvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

4,5-Dihydro-3-propylamino-5-oxo-1-(2,4,6-trichloro-phenyl)-1H-pyrazole (21.9 g, 68.3 mmol) was dissolved in a mixture of tetrahydrofuran (170 ml) and pyridine (34 ml) and the solution was cooled in an ice-bath. m-Nitrobenzoyl chloride (25.35 g, 136.7 mmol) was dissolved in tetrahydrofuran (40 ml) and the solution was added dropwise to the stirred, cooled mixture. Stirring was continued at room temperature for 19 hrs. A further quantity of m-nitrobenzoyl chloride (10%) was added and the mixture was stirred for 2 hrs to complete the reaction. The mixture was poured into dilute hydrochloric acid (31) and the oily solid was extracted with ethyl acetate. The extract was washed with water and dried (MgSO4). The solvent was removed by evaporation and replaced with ethanol (300 ml). A solution of sodium hydroxide (13.7 g, 324 mmol) in water (40 ml) was added dropwise and the mixture was stirred for 1 hr. The mixture was poured into dilute hydrochloric acid (21) and the resulting oil was extracted with ethyl acetate. The extract was washed with water and dried (MgSO4). The solvent was evaporated under reduced pressure to give a resin, 33.0 g, ca 100%. This was used in the next stage without purification.

Workup

  1. temperaturethe solution was cooled in an ice-bath
  2. additionthe solution was added dropwise to the stirred
  3. temperaturecooled mixture
  4. stirringthe mixture was stirred for 2 hrs
  5. customthe reaction
  6. extractionthe oily solid was extracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried (MgSO4)
  9. customThe solvent was removed by evaporation
  10. stirringthe mixture was stirred for 1 hr
  11. extractionthe resulting oil was extracted with ethyl acetate
  12. washThe extract was washed with water
  13. dry with materialdried (MgSO4)
  14. customThe solvent was evaporated under reduced pressure
  15. customto give a resin, 33.0 g, ca 100%
  16. customThis was used in the next stage without purification

Sources & evidence

ORD record
ord-be1fd0a6bc57461abaaac9bebe6f715f
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06010837

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes