Potassium Carbonate → HCID 22666129, compound

HRID 2416958Notes

Reaction equation

HRID 2416958 reaction equation
C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]C(O)=O.C(=O)([O-])[O-].[K+].[K+].BrCCCCCCC[C:43]([N:45]=[N+]=[N-])=[O:44].[CH:48]([C:51]1[CH:57]=[CH:56][CH:55]=[C:54]([CH:58]([CH3:60])[CH3:59])[C:52]=1[NH2:53])([CH3:50])[CH3:49]>O.C(Cl)(Cl)Cl.CN(C=O)C>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:45][C:43]([NH:53][C:52]1[C:51]([CH:48]([CH3:50])[CH3:49])=[CH:57][CH:56]=[CH:55][C:54]=1[CH:58]([CH3:60])[CH3:59])=[O:44]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 32484DiisopropylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 5482758-Bromooctanoic acidHCID 54317182HCID 54317182, compound

Product 1

HCID 22666129HCID 22666129, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

DPPA (123 mg, 0.45 mmols) was added to a DMF (1 ml) solution of 8-bromooctanoic acid (100 mg, 0.45 mmols) and potassium carbonate (68 mg, 0.49 mmols), and stirred at room temperature for 3 hours. The reaction mixture was diluted with water, and extracted with ether. The organic layer was washed with water, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. A chloroform (2 ml) solution of the resulting 8-bromooctanoic acid azide (95 mg, 0.38 mmols) was heated under reflux for 30 minutes, to which was added a chloroform (1 ml) solution of 2,6-diisopropylaniline (68 mg, 0.38 mmols), and heated under reflux for further 15 hours. After the reaction, the solvent was evaporated, and the residue was purified through preparative thin-layer chromatography (developer: chloroform/methanol=20/1) to obtain 112 mg (yield: 63%) of N-(7-bromoheptyl)-N′-(2,6-diisopropylphenyl) urea as colorless powdery crystals.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. temperatureunder reflux for 30 minutes, to which
  6. temperatureheated
  7. temperatureunder reflux for further 15 hours
  8. customAfter the reaction
  9. customthe solvent was evaporated
  10. customthe residue was purified through preparative thin-layer chromatography (developer: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-3175a5289e1440fc9505c67f5bd2d5a4
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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