Dicyclohexylcarbodiimide → HCID 13146238, compound

HRID 2413213Notes

Reaction equation

HRID 2413213 reaction equation
[C:1]([OH:17])(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:48](=[NH:50])[NH2:49])[CH:44]=2)[CH:39]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:17][C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[C:43]([C:48](=[NH:49])[NH2:50])[CH:44]=2)[CH:39]=1)(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13849Pentadecanoic AcidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146238HCID 13146238, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4.3 g of n-pentadecanoic 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 a methanol-dimethylformamide mixture, freed from the insolubles by filtration, and concentrated under reduced pressure. The crystals formed upon addition of ethyl ether were recrystallized from methanol to obtain 3.0 g of a white powder of 6-amidino-2-naphthyl pentadecanoate 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 a methanol-dimethylformamide mixture
  5. filtrationfreed from the insolubles by filtration
  6. concentrationconcentrated under reduced pressure
  7. customThe crystals formed upon addition of ethyl ether
  8. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-032b314bfc874686bf2d01242ffb408a
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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