Hydrogen iodide → HCID 86733206, compound

HRID 1605014Notes

Reaction equation

HRID 1605014 reaction equation
[BH4-].[Na+].[I-:3].[CH3:4][NH+:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[N:6]1[CH3:23].I>C(O)(C)C.O>[IH:3].[CH3:4][N:5]1[CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[N:6]1[CH3:23]

Participants

6

Reactant 3

HCID 24841Hydrogen iodideHCID 4311764Sodium borohydrideHCID 86733207HCID 86733207, compound

Product 1

HCID 86733206HCID 86733206, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

Sodium borohydride (76 g, 0.02 mole) is added to a slurry of 1,2-dimethyl-3-(m-fluorophenyl)-5-phenyl-pyrazolinium iodide (4 g, 0.01 mole) in isopropanol (125 ml). After becoming homogeneous, the reaction mixture is stirred for 24 hours. Water (10 ml) is then slowly added. Isopropanol is removed on a rotary evaporator and resultant residue is slurried in water (50 ml) and extracted with chloroform. Evaporation of the organic layer yields an oil, which is slurried in water. Aqueous hydriodic acid (5 ml, 46-50%) is next added. After stirring for one hour, resulting solid is filtered and dried to give 3.3 g, 83%; melting point 187°-189°C.

Workup

  1. customIsopropanol is removed on a rotary evaporator and resultant residue
  2. extractionextracted with chloroform
  3. customEvaporation of the organic layer
  4. customyields an oil, which
  5. stirringAfter stirring for one hour
  6. customresulting solid
  7. filtrationis filtered
  8. customdried
  9. customto give 3.3 g, 83%

Sources & evidence

ORD record
ord-a9b966a062be4e458eb539bd4b5e78fd
Source dataset
uspto-grants-1976_04
Patent number
US03948936

Reaction notes

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