Hydrochloric Acid → HCID 178456949, compound

HRID 848955Notes

Reaction equation

HRID 848955 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](C(C)C(N)=O)[CH2:3]1.CO.Cl.O>O1CCCC1>[CH2:4]([NH:5][C:4]1[CH2:3][C:2](=[O: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]=1)[CH2:3][CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 70294282HCID 70294282, compound

Product 1

HCID 178456949HCID 178456949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl propionamide (31.93 g, 95.6 mmol) was dissolved in dry tetrahydrofuran (400 ml) with warming and the solution was cooled to 10° C. with stirring. Borane dimethylsulfide complex (10M, 32 ml, 320 mmole) was added dropwise by syringe through a septum cap. The reaction mixture was heated on a steam-bath for 12 hrs then it was cooled in an ice-bath. Methanol (32 ml) was added dropwise and the mixture was stirred for 1 hr until the effervescence had subsided. Concentrated hydrochloric acid (7 ml) was added to give a clear solution. This was poured into water (100 ml) and the mixture was extracted twice with ethyl acetate (100 ml). The extracts were combined, washed with water and dried (MgSO4). Evaporation of the solvent left a yellow oil which was dried under vacuum for 2 hrs. The crude product (37.1 g) was purified by column chromatography on silica gel, eluting with a 2:1 mixture of ethyl acetate and 60-80 petroleum ether to give a pale yellow oil which solidified on standing, 22.0 g, 72%.

Workup

  1. temperaturewith warming
  2. additionBorane dimethylsulfide complex (10M, 32 ml, 320 mmole) was added dropwise by syringe through a septum
  3. customcap
  4. temperatureThe reaction mixture was heated on a steam-bath for 12 hrs
  5. temperatureit was cooled in an ice-bath
  6. stirringthe mixture was stirred for 1 hr until the effervescence
  7. customto give a clear solution
  8. extractionthe mixture was extracted twice with ethyl acetate (100 ml)
  9. washwashed with water
  10. dry with materialdried (MgSO4)
  11. customEvaporation of the solvent
  12. waitleft a yellow oil which
  13. customwas dried under vacuum for 2 hrs
  14. customThe crude product (37.1 g) was purified by column chromatography on silica gel
  15. washeluting with a 2:1 mixture of ethyl acetate and 60-80 petroleum ether
  16. customto give a pale yellow oil which

Sources & evidence

ORD record
ord-8b7485b02ad442a6a98341ab8965a721
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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