Hydrochloric Acid → 6-Amidino-1-methoxycarbonyl-2-naphthyl 4-aminoiminomethylaminobenzoate

HRID 1419245Notes

Reaction equation

HRID 1419245 reaction equation
[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.Cl.[C:15]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24]([C:28]([O:30][CH3:31])=[O:29])=[C:23](O)[CH:22]=[CH:21]2)(=[NH:17])[NH2:16].CS([O-])(=O)=O.C1CCC(N=C=NC2CCCCC2)CC1>N1C=CC=CC=1>[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][CH:27]=[C:18]([C:15](=[NH:16])[NH2:17])[CH:19]=3)[C:24]=2[C:28]([O:30][CH3:31])=[O:29])=[O:10])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 85257MethanesulfonateHCID 1356130286-Amidino-1-methoxycarbonyl-2-naphtholHCID 178514393HCID 178514393, compound

Product 1

HCID 1784989726-Amidino-1-methoxycarbonyl-2-naphthyl 4-aminoiminomethylaminobenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

50 Milliliters of anhydrous pyridine was added to 1.9 g of 4-aminoiminomethylaminobenzoic acid.hydro-chloride, 3.0 g of of 6-amidino-1-methoxycarbonyl-2-naphthol.methanesulfonate, and 2.2 g of DCC, followed by stirring for 2 hours under cooling with ice and 24 hours at room temperature. The precipitate was collected by filtration and washed with a small amount of pyridine. To the collected precipitate was added 30 ml of water, followed by stirring for 1 hour. Insoluble matter was filtered off and the filtrate was added dropwise to 100 ml of saturated aqueous sodium bicarbonate solution, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration and washed with a small amount of water and acetone. To the collected precipitate were added 15 ml of methanol and 2.2 ml of methanesulfonic acid. The resulting solution was added dropwise to 300 ml of ether, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration and washed with a small amount of acetone to obtain 2.46 g of the desired product.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with a small amount of pyridine
  3. additionTo the collected precipitate was added 30 ml of water
  4. stirringby stirring for 1 hour
  5. filtrationInsoluble matter was filtered off
  6. additionthe filtrate was added dropwise to 100 ml of saturated aqueous sodium bicarbonate solution
  7. stirringby stirring for 24 hours
  8. temperatureunder cooling with ice
  9. filtrationThen, the precipitate was collected by filtration
  10. washwashed with a small amount of water and acetone
  11. additionTo the collected precipitate were added 15 ml of methanol and 2.2 ml of methanesulfonic acid
  12. additionThe resulting solution was added dropwise to 300 ml of ether
  13. stirringby stirring for 24 hours
  14. temperatureunder cooling with ice
  15. filtrationThen, the precipitate was collected by filtration
  16. washwashed with a small amount of acetone

Sources & evidence

ORD record
ord-49cfdca8668749a69b064e4afe633647
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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