Sodium Iodide → HCID 178420497, compound

HRID 2095199Notes

Reaction equation

HRID 2095199 reaction equation
[C:1]1([C:7]2[C:8](=[N:13][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([NH2:12])=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl.Cl[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C(#N)C>[N:33]1([CH2:32][CH2:31][NH:12][C:9]2[C:8](=[N:13][NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:11][N:10]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178509135HCID 178509135, compound

Product 1

HCID 178420497HCID 178420497, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Phenyl-4-(phenylhydrazono)-4H-pyrazol-3-ylamine (65 mg, 0.25 mmol) was dissolved in 5 mL of acetonitrile. Potassium carbonate (70 mg, 0.5 mmol) and a catalytic amount of sodium iodide were added and the solution was heated to reflux. 4-(2-chloroethyl)morpholine hyrdochloride (50 mg, 0.25 mmol) was added in small portions over 30 min. After heating at reflux for 6 hours, the reaction was allowed to cool to ambient temperature and was stirred overnight. Some of the residual 4-(2-chloroethyl)morpholine was removed by stirring the solution over 50 mg of polystyrene bound thiophenol with 1 drop of diethylisopropylamine. The solution was filtered through celite and evaporated to a tan solid. The solid was then dissolved in ethyl acetate and precipitated with hexanes. The solid was isolated by filtration and air dried. The material was purified by column chromatography (CH2Cl2:MeOH=10:1) to yield two fractions in amounts of 28 mg and 35 mg (total 67%). 1H NMR (ppm, 200 MHz, CDCl3) δ 2.60 (t, 4H), 2.80 (t, 2H), 3.70 (t, 4H), 4.18 (t, 2H), 7.25-7.50 (m, 8H), 7.78 (d, 2H), 8.15 (d, 2H).

Workup

  1. temperaturethe solution was heated to reflux
  2. temperatureAfter heating
  3. temperatureat reflux for 6 hours
  4. customSome of the residual 4-(2-chloroethyl)morpholine was removed
  5. stirringby stirring the solution over 50 mg of polystyrene
  6. filtrationThe solution was filtered through celite
  7. customevaporated to a tan solid
  8. dissolutionThe solid was then dissolved in ethyl acetate
  9. customprecipitated with hexanes
  10. customThe solid was isolated by filtration and air
  11. customdried
  12. customThe material was purified by column chromatography (CH2Cl2:MeOH=10:1)
  13. customto yield two fractions in amounts of 28 mg and 35 mg (total 67%)

Sources & evidence

ORD record
ord-7b1e86ec08cb4f7e8178428d914c5378
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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