Potassium Carbonate → HCID 68452419, compound

HRID 389230Notes

Reaction equation

HRID 389230 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:31])[C:19]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)=O>O1CCCC1>[C:3]1([C:2]2[NH:9][C:18]([CH3:31])=[C:19]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80289Benzamidine, hydrochlorideHCID 125874062-Bromo-1-(naphthalen-2-yl)propan-1-one2×

Product 1

HCID 68452419HCID 68452419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension consisting of 45.1 g (0.288 mol) of benzamidine hydrochloride, 119.4 g (0.864 mol) of potassium carbonate, and 240 mL of tetrahydrofuran was heated under reflux for one hour, and the foregoing toluene solution of 2-bromo-2′-propionaphthone was added dropwise over 40 minutes. After completion of addition, heating under reflux was continued for 2 hours. Next, the reaction mixture was concentrated in vacuo, the resulting concentrate was diluted with 200 mL of toluene, and the solution was poured into 600 mL of water. The mixture was stirred to precipitate a solid. This solid was collected by filtration, successively washed with toluene and water, and then dried to obtain a crude crystal as a desired material. This crude crystal was recrystallized from acetonitrile to obtain 55.0 g (yield: 67.2%) of a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. additionAfter completion of addition
  4. temperatureheating
  5. temperatureunder reflux
  6. concentrationNext, the reaction mixture was concentrated in vacuo
  7. concentrationthe resulting concentrate
  8. additionwas diluted with 200 mL of toluene
  9. additionthe solution was poured into 600 mL of water
  10. customto precipitate a solid
  11. filtrationThis solid was collected by filtration
  12. washsuccessively washed with toluene and water
  13. customdried

Sources & evidence

ORD record
ord-a838cc41142f43ddb77abb888b94ea4d
Source dataset
uspto-grants-2013_02
Patent number
US08378116B2

Reaction notes

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