Pyridine → HCID 13178456, compound

HRID 1981438Notes

Reaction equation

HRID 1981438 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O)(=O)=O.CS(O)(=O)=O.[C:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([NH2:27])[CH:21]=1)(=[NH:19])[NH2:18].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O:39][CH2:40][CH3:41])C>>[C:28]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:17](=[NH:18])[NH2:19])=[CH:21][C:22]=1[NH:27][C:40](=[O:39])[C:41]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 135598727HCID 135598727, compound

Product 1

HCID 13178456HCID 13178456, compound

Procedure

Into 30 ml of pyridine, was dissolved 1.7 g of 4-amidino-2-aminophenol dimethanesulfonate. to the solution, while being cooled in ice and stirred, was added 1.8 g of benzoyl chloride. The mixture was stirred for 30 minutes while cooling in ice and 2 hours at room temperature. The reaction mixture was admixed with about 100 ml of ethyl ether to allow a colorless oily substance to separate out. The solvent was removed by decantation and the residue was dissolved in a small volume of ethanol. Upon addition of a saturated aqueous sodium hydrogencarbonate solution, colorless crystals of 4-amidino-2-benzoylaminophenyl benzoate carbonate were precipitated. The crystals were collected by filtration, washed with water, then with acetone, and suspended in ethanol. On addition of methanesulfonic acid, the suspension turned into a clear solution. Ethyl ether was added to the solution to precipitate crystals. The crystals were collected by filtration and recrystallized from an ethanol-ethyl ether mixture to obtain 1.4 g of colorless crystals of 4-amidino-2-benzoylaminophenyl benzoate methanesulfonate.

Workup

  1. temperatureto the solution, while being cooled in ice
  2. stirringThe mixture was stirred for 30 minutes
  3. customto separate out
  4. customThe solvent was removed by decantation
  5. dissolutionthe residue was dissolved in a small volume of ethanol
  6. additionUpon addition of a saturated aqueous sodium hydrogencarbonate solution, colorless crystals of 4-amidino-2-benzoylaminophenyl benzoate carbonate
  7. customwere precipitated
  8. filtrationThe crystals were collected by filtration
  9. washwashed with water
  10. additionOn addition of methanesulfonic acid
  11. additionEthyl ether was added to the solution
  12. customto precipitate crystals
  13. filtrationThe crystals were collected by filtration
  14. customrecrystallized from an ethanol-ethyl ether mixture

Sources & evidence

ORD record
ord-1f288318756840cdb34544cde3f82eac
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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