Acetonitrile → HCID 18698803, compound

HRID 2289614Notes

Reaction equation

HRID 2289614 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH2:8][CH2:9][CH3:10].[N:12]1([C:18]2[N:25]3[C:21](=[N:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=43)[S:20][N:19]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(#N)C>C1COCC1.CS(C)=O>[CH2:7]([N:15]1[CH2:14][CH2:13][N:12]([C:18]2[N:25]3[C:21](=[N:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=43)[S:20][N:19]=2)[CH2:17][CH2:16]1)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 23303032HCID 23303032, compound

Product 1

HCID 18698803HCID 18698803, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of potassium carbonate (700 mg, 5.06 mmol), butyl bromide (0.43 mL, 0.4 mmol), 3-piperazinyl-1,2,4-thiadiazolo[4,5-a]benzimidazole (798 mg, 3.07 mmol) in THF (15 mL) and DMSO (2 mL) was refluxed for 16 h. The solution was evaporated to dryness, the residue partitioned between dichloromethane and water. The organic layer was washed five times with water, dried over sodium sulfate and evaporated to give an oil. This oil was mixed with acetonitrile, an insoluble solid was formed which was filtered (595 mg). The solid was purified by chromatography to give the title compound which was recrystallized from hexane (5:95) (440 mg, 41%).

Workup

  1. temperaturewas refluxed for 16 h
  2. customThe solution was evaporated to dryness
  3. customthe residue partitioned between dichloromethane and water
  4. washThe organic layer was washed five times with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give an oil
  8. customan insoluble solid was formed which
  9. filtrationwas filtered (595 mg)
  10. customThe solid was purified by chromatography

Sources & evidence

ORD record
ord-f076a672fc444dec8e6e9e7bda09e822
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

Loading…