Isopropanol → HCID 13106789, compound

HRID 371764Notes

Reaction equation

HRID 371764 reaction equation
[BH4-].[Na+].C(O)(C)C.COS([O-])(=O)=O.[CH3:13][N+:14]1[N:15]([CH3:31])[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH3:31][N:15]1[CH:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]1[CH3:13]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 39424Difenzoquat metilsulfateHCID 4311764Sodium borohydride2×

Product 1

HCID 13106789HCID 13106789, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (19 g, 0.5 mole) is added portionwise to an isopropanol (1 liter) solution of 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate (40.1 g, 0.25 mole). The reaction is allowed to stir at room temperature for 3 days; then additional sodium borohydride (9 g, 0.25 mole) is added, and the reaction is heated to reflux with stirring and maintained there for 7 hours. The reaction mixture is cooled to room temperature and water (100 ml) is added over a 11/2-hour period. After stirring for 2 hours, the isopropanol is removed on a rotary evaporator, and the resulting paste slurried in water and extracted with diethyl ether. Evaporation of the ether layer gives the pyrazolidine as a viscous oil; 48.3 g, 72%, and analyzed as its HCl salt.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux
  3. stirringwith stirring
  4. temperaturemaintained there for 7 hours
  5. temperatureThe reaction mixture is cooled to room temperature
  6. stirringAfter stirring for 2 hours
  7. customthe isopropanol is removed on a rotary evaporator
  8. extractionextracted with diethyl ether
  9. customEvaporation of the ether layer

Sources & evidence

ORD record
ord-db5cddd044a349d3a91b6d5f5fe2388f
Source dataset
uspto-grants-1978_05
Patent number
US04087612

Reaction notes

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