Acetonitrile → HCID 1947910, compound

HRID 422905Notes

Reaction equation

HRID 422905 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH2:18]([NH:22][S:1]([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8007ButylamineHCID 11430Potassium CarbonateHCID 11801Dansyl chloride

Product 1

HCID 1947910HCID 1947910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One equivalent of dansyl chloride (7) was added to a solution containing 2 equivalents of both butylamine and potassium carbonate in 1:1 acetonitrile:water. Solution was stirred at room temperature for 1.5 hrs. Acetonitrile was then removed and water residue extracted with ethyl acetate. The organic solution washed with 5% sodium bicarbonate, 2M citric acid and brine. Solution was dried over magnesium sulfate, filtered and solvent removed by flash evaporation. Crude was dissolved in minimal amount of ethyl acetate and hexane was added until cloudiness. Solution was stored in the refrigerator for 2 hrs. The precipitate was collected by suction filtration, washed with hexane and dried on the pump. ESI-MS and 1H-NMR were consistent with structure 8, which is (n-butyl dansylamide; BDA): 1H-NMR (CDCl3, =ppm): 8.55 (1H, d); 8.30 (2H, dd); 7.55 (2H, m); 7.20 (1H, d); 4.80 (1H, t); 2.90 (8H, m); 1.35 (2H, m). 1.20 (2H, m); 0.70 (3H, t). ESI-MS: Calc. m/z=306.4. Found m/z+H+=307.4.

Workup

  1. customAcetonitrile was then removed
  2. extractionwater residue extracted with ethyl acetate
  3. washThe organic solution washed with 5% sodium bicarbonate, 2M citric acid and brine
  4. dry with materialSolution was dried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed by flash evaporation
  7. dissolutionCrude was dissolved in minimal amount of ethyl acetate and hexane
  8. additionwas added until cloudiness
  9. waitSolution was stored in the refrigerator for 2 hrs
  10. filtrationThe precipitate was collected by suction filtration
  11. washwashed with hexane
  12. customdried on the pump

Sources & evidence

ORD record
ord-7da9a6773da240c2b0bcd75e6bbf6158
Source dataset
uspto-grants-2012_01
Patent number
US08101666B2

Reaction notes

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