Hydrochloric Acid → HCID 136365336, compound

HRID 1419246Notes

Reaction equation

HRID 1419246 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH2:14][C:15](=[O:17])N)=[C:9]([OH:18])[CH:8]=[CH:7]2)(=[NH:3])[NH2:2].Cl.C(=O)(O)[O-:21].[Na+]>O>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH2:14][C:15]([OH:21])=[O:17])=[C:9]([OH:18])[CH:8]=[CH:7]2)(=[NH:3])[NH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 136171528HCID 136171528, compound

Product 1

HCID 136365336HCID 136365336, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To 12.4 g of 6-amidino-1-carbamoylmethyl-2-naphthol was added 370 g of 25% hydrochloric acid, followed by stirring at 70° C. for 2.5 hours. After cooling with water, the precipitate was collected by filtration and washed with 80 g of 15% hydrochloric acid. The collected precipitate was added to a solution prepared by adding 200 ml of water to 10 g of sodium bicarbonate, followed by stirring for 1 hour at room temperature, and the resulting precipitate was collected by filtration and washed with water. This collected precipitate was added to a solution of 13 ml of methanesulfonic acid in 180 ml of water to dissolve the precipitate at 50° C. Furthermore, 1.0 g of active carbon was added to the solution, followed by stirring for 1 hour at room temperature. Thereafter, insoluble matter was filtered off and the filtrate was concentrated to 90 ml under reduced pressure. This solution was stirred for 24 hours under cooling with water. Then, the precipitate was collected by filtration and washed with a small amount of acetone and ether to obtain 12.3 g of the desired product.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with 80 g of 15% hydrochloric acid
  3. additionThe collected precipitate was added to a solution
  4. customprepared
  5. stirringby stirring for 1 hour at room temperature
  6. filtrationthe resulting precipitate was collected by filtration
  7. washwashed with water
  8. additionThis collected precipitate was added to a solution of 13 ml of methanesulfonic acid in 180 ml of water
  9. dissolutionto dissolve the precipitate at 50° C
  10. additionFurthermore, 1.0 g of active carbon was added to the solution
  11. stirringby stirring for 1 hour at room temperature
  12. filtrationThereafter, insoluble matter was filtered off
  13. concentrationthe filtrate was concentrated to 90 ml under reduced pressure
  14. stirringThis solution was stirred for 24 hours
  15. temperatureunder cooling with water
  16. filtrationThen, the precipitate was collected by filtration
  17. washwashed with a small amount of acetone and ether

Sources & evidence

ORD record
ord-75c278300cb745dd8969d5880fc17f9c
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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