Dicyclohexylcarbodiimide → HCID 13146242, compound

HRID 2413215Notes

Reaction equation

HRID 2413215 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:41])[NH2:40])[CH:35]=2)[CH:30]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:8][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:40])[NH2:41])[CH:35]=2)[CH:30]=1)(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 643460Sorbic AcidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146242HCID 13146242, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.0 g of sorbic acid in 50 ml of anhydrous pyridine, while being cooled in ice, was added 4.4 g of DCC. After stirring for 30 minutes, 5.0 g of 6-amidino-2-naphthol methanesulfonate was added to the mixture and further stirred overnight at room temperature. The precipitate was collected by filtration, washed with ethyl ether, then with acetone, dissolved in methanol, and filtered to remove the insolubles. The filtrate was concentrated under reduced pressure and recrystallized from an ethanol-methanol mixture to yeild 2.4 g of colorless granular crystals 6-amidino-2-naphthyl sorbate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethyl ether
  4. dissolutionwith acetone, dissolved in methanol
  5. filtrationfiltered
  6. customto remove the insolubles
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customrecrystallized from an ethanol-methanol mixture to yeild 2.4 g of colorless granular crystals 6-amidino-2-naphthyl sorbate methanesulfonate

Sources & evidence

ORD record
ord-c6da5cb4afc3408daf552098f548669f
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

Loading…