Hydrochloric Acid → HCID 178482490, compound

HRID 848951Notes

Reaction equation

HRID 848951 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]([NH:16][CH:17]=O)[CH2:3]1.CO.Cl.O>O1CCCC1>[CH3:17][NH:16][C:4]1[CH2:3][C:2](=[O: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]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 19369068HCID 19369068, compound

Product 1

HCID 178482490HCID 178482490, 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 formamide (39.6 g, 129.2 mmole) was dissolved in dry tetrahydrofuran (500 ml) with warming and then cooled to 10° C. with stirring. Borane dimethylsulfide complex (10M, 80 ml, 800 mmole) was added dropwise by syringe through a septum cap. The reaction mixture was heated on a steam bath for ca 12 hrs (overnight), cooled in an ice bath, methanol (150 ml) added dropwise and the mixture stirred for 1 hr until the effervescence had subsided. Concentrated hydrochloric acid (30 ml) was then added to give a clear solution. This was poured into water (51) and extracted with ethyl acetate (×2) and the extract washed and dried (MgSO4). Evaporation of the solvent left a white glass which was dried under vacuum for 2 hrs. The yield of product was 33.4 g, 88%.

Workup

  1. temperaturewith warming
  2. additionBorane dimethylsulfide complex (10M, 80 ml, 800 mmole) was added dropwise by syringe through a septum
  3. customcap
  4. temperatureThe reaction mixture was heated on a steam bath for ca 12 hrs (overnight)
  5. temperaturecooled in an ice bath
  6. stirringthe mixture stirred for 1 hr until the effervescence
  7. customto give a clear solution
  8. extractionextracted with ethyl acetate (×2)
  9. washthe extract washed
  10. dry with materialdried (MgSO4)
  11. customEvaporation of the solvent
  12. waitleft a white glass which
  13. customwas dried under vacuum for 2 hrs

Sources & evidence

ORD record
ord-5d64ae59ca38424bad57f1b36aebd389
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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