Ethyl Acetate → HCID 86739496, compound

HRID 371437Notes

Reaction equation

HRID 371437 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16](=[NH:18])[NH2:17])[CH:12]=2)[CH:7]=1)(=[O:4])=[O:3].[C:19](Cl)(=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:19]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16](=[NH:18])[NH2:17])[CH:12]=2)[CH:7]=1)(=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 660233-Phenylprop-2-enoyl chlorideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 86739496HCID 86739496, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 9.9 g of 6-amidino-2-naphthol methanesulfonate in 100 ml of anhydrous pyridine, while being cooled in ice and stirred, was added 5.8 g of cinnamoyl chloride. After having been stirred overnight at room temperature, the mixture was admixed with ethyl acetate and the resulting precipitate was collected by filtration. The precipitate was suspended in methanol, mixed with a saturated aqueous sodium hydrogencarbonate solution with stirring, and the precipitate was collected by filtration. After having been washed with water and acetone, the precipitate was suspended in methanol and mixed with methanesulfonic acid. After having been stirred for same time, the mixture was admixed with ethyl ether, the precipitate was collected by filtration and recrystallized from a methanol-ethyl ether mixture to obtain 7.1 g of 6-amidino-2-naphthyl cinnamate methanesulfonate.

Workup

  1. stirringAfter having been stirred overnight at room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. additionmixed with a saturated aqueous sodium hydrogencarbonate solution
  4. stirringwith stirring
  5. filtrationthe precipitate was collected by filtration
  6. washAfter having been washed with water and acetone
  7. additionmixed with methanesulfonic acid
  8. stirringAfter having been stirred for same time
  9. filtrationthe precipitate was collected by filtration
  10. customrecrystallized from a methanol-ethyl ether mixture

Sources & evidence

ORD record
ord-ad6397d41dc64c7496c7eca154282097
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

Loading…