Potassium Iodide → HCID 86718549, compound

HRID 1485026Notes

Reaction equation

HRID 1485026 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:19]1[C:23](N)=[CH:22][CH:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N([O-])=O.[Na+].[I-:29].[K+]>C(#N)C.O.C([O-])(O)=O.[Na+]>[CH2:12]([N:19]1[C:23]([I:29])=[CH:22][CH:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 6101p-Toluenesulfonic acidHCID 770611-Benzyl-1H-pyrazol-5-amineHCID 23668193Sodium Nitrite

Product 1

HCID 86718549HCID 86718549, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
12.5 °C

Procedure

p-Toluenesulfonic acid (29.82 g; 0.17 mol) was stirred in 150 ml ACN. 2-Benzyl-2H-pyrazol-3-ylamine (10.0 g; 0.06 mol) was added and cooled down to 10-15° C. Sodium nitrite (7.97 g; 0.12 mol) was dissolved in 15.0 ml water and added. The resulting mixture was stirred for 1 hour at 0° C. In 30 ml of water was dissolved potassium iodide (23.96 g; 0.14 mol) and added at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours. It was diluted with 100 ml water and neutralized with NaHCO3 solution, then extracted with DCM. The organic layers were pooled and washed with sodium thiosulfate, dried and evaporated. The crude material was purified with normal phase chromatography (2% EtOAc/Hexane).

Workup

  1. additionadded
  2. additionadded at 0° C
  3. stirringThe reaction mixture was stirred at ambient temperature for 6 hours
  4. extractionextracted with DCM
  5. washwashed with sodium thiosulfate
  6. customdried
  7. customevaporated
  8. customThe crude material was purified with normal phase chromatography (2% EtOAc/Hexane)

Sources & evidence

ORD record
ord-5b910fb823414625b95b6588419071a1
Source dataset
uspto-grants-2016_08
Patent number
US09422290B2

Reaction notes

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