Hydrochloric Acid → HCID 19369066, compound

HRID 848952Notes

Reaction equation

HRID 848952 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([N:16]([CH3:26])[C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=2)[CH2:3]1.[C:27]([C:32]1[CH:42]=[C:41]([C:43]([CH2:46][CH3:47])([CH3:45])[CH3:44])[CH:40]=[CH:39][C:33]=1[O:34][CH2:35][C:36](Cl)=[O:37])([CH2:30][CH3:31])([CH3:29])[CH3:28].Cl.[OH-].[Na+]>O1CCCC1.N1C=CC=CC=1.O>[O:1]=[C:2]1[N:6]([C:7]2[C:8]([Cl:15])=[CH:9][C:10]([Cl:14])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([N:16]([CH3:26])[C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:36](=[O:37])[CH2:35][O:34][C:33]3[CH:39]=[CH:40][C:41]([C:43]([CH2:46][CH3:47])([CH3:45])[CH3:44])=[CH:42][C:32]=3[C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH:19]=2)[CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66612(2,4-Bis(1,1-dimethylpropyl)phenoxy)acetyl chlorideHCID 19369063HCID 19369063, compound

Product 1

HCID 19369066HCID 19369066, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-methyl-3-aminobenzamide (8.2 g, 19.9 mmole) was dissolved in a mixture of tetrahydrofuran (100 ml) and pyridine (20 ml) and cooled in an ice bath. 2,4-Di-t-pentylphenoxyacetyl chloride (20.5 mmole) was dissolved in tetrahydrofuran (20 ml) and added dropwise to the stirred mixture. Stirring was continued for 1 hr and the mixture was then poured into stirred dilute hydrochloric acid (1.51), the oil extracted into ethyl acetate and the extract washed and dried. The solvent was removed by evaporation and replaced with ethanol (100 ml). A solution of sodium hydroxide (0.8 g, 20 mmole) in water (5 ml) was added dropwise and the mixture stirred for 15 min. The oil gradually dissolved and a solid gradually formed. The mixture was poured into dilute hydrochloric acid (11) and the pale orange solid filtered off washed and dried. The solid was chromatographed on silica gel using 1:1 60-80 petroleum ether: ethyl acetate as eluent to give the product as a white glass, 6.9 g, 50%.

Workup

  1. temperaturecooled in an ice bath
  2. additionadded dropwise to the stirred mixture
  3. additionthe mixture was then poured
  4. extractionthe oil extracted into ethyl acetate
  5. washthe extract washed
  6. customdried
  7. customThe solvent was removed by evaporation
  8. stirringthe mixture stirred for 15 min
  9. dissolutionThe oil gradually dissolved
  10. customa solid gradually formed
  11. filtrationthe pale orange solid filtered off
  12. washwashed
  13. customdried
  14. customThe solid was chromatographed on silica gel using 1:1 60-80 petroleum ether

Sources & evidence

ORD record
ord-b2a3a1d2436d40c481d5c5b641abc8bc
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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