Dicyclohexylcarbodiimide → HCID 178512532, compound

HRID 1419224Notes

Reaction equation

HRID 1419224 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3].CS([O-])(=O)=O.Cl.[C:20]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29]([CH2:33][C:34](=[O:36])[NH2:35])=[C:28](O)[CH:27]=[CH:26]2)(=[NH:22])[NH2:21].C1CCC(N=C=NC2CCCCC2)CC1>CO.N1C=CC=CC=1>[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:28]2[CH:27]=[CH:26][C:25]3[C:30](=[CH:31][CH:32]=[C:23]([C:20](=[NH:21])[NH2:22])[CH:24]=3)[C:29]=2[CH2:33][C:34](=[O:36])[NH2:35])=[O:10])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 85257MethanesulfonateHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178512548HCID 178512548, compound

Product 1

HCID 178512532HCID 178512532, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

100 Milliliters of 20% hydrous pyridine was added to 3.0 g of 4-guanidinobenzoic acid.methanesulfonate, 3.0 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride and 4.5 g of DCC, followed by stirring for 2 hours under cooling with ice and then 2 days at room temperature. The precipitate was filtered and 1 g of active carbon was added to the filtrate, followed by stirring for 30 minutes under cooling with ice, and insoluble matter was filtered off. The filtrate was slowly added dropwise to 4 liters of ether under cooling with ice, followed by stirring for 2 hours. The precipitate was collected by filtration and washed with 100 ml of acetone to obtain a crude product. Then, the product was dissolved in 150 ml of methanol. Thereafter, 2.5 g of active carbon was added to the solution, followed by stirring for 30 minutes under cooling with ice, and insoluble matter was filtered off. The filtrate was slowly added dropwise to 1 liter of acetone under cooling with ice, followed by stirring for 2 hours. The precipitate was collected by filtration to obtain 2.9 g of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom2 days
  3. customat room temperature
  4. filtrationThe precipitate was filtered
  5. addition1 g of active carbon was added to the filtrate
  6. stirringby stirring for 30 minutes
  7. temperatureunder cooling with ice, and insoluble matter
  8. filtrationwas filtered off
  9. additionThe filtrate was slowly added dropwise to 4 liters of ether
  10. temperatureunder cooling with ice
  11. stirringby stirring for 2 hours
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with 100 ml of acetone
  14. customto obtain a crude product
  15. additionThereafter, 2.5 g of active carbon was added to the solution
  16. stirringby stirring for 30 minutes
  17. temperatureunder cooling with ice, and insoluble matter
  18. filtrationwas filtered off
  19. additionThe filtrate was slowly added dropwise to 1 liter of acetone
  20. temperatureunder cooling with ice
  21. stirringby stirring for 2 hours
  22. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-698169006f1644d9ac9f68003bcfa197
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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