Lauric Acid → HCID 13146236, compound

HRID 2413212Notes

Reaction equation

HRID 2413212 reaction equation
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:45](=[NH:47])[NH2:46])[CH:41]=2)[CH:36]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:14][C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:45](=[NH:46])[NH2:47])[CH:41]=2)[CH:36]=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 3893Lauric AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146236HCID 13146236, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.6 g of lauric 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 ether, then with acetone, dissolved in methanol, freed from the insolubles by filtration, concentrated under reduced pressure, and recrystallized from ethanol to yield 1.2 g of white crystals of 6-amidino-2-naphthyl laurate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ether
  4. dissolutionwith acetone, dissolved in methanol
  5. filtrationfreed from the insolubles by filtration
  6. concentrationconcentrated under reduced pressure
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e1aef1866bd644ddb97de7a78fcf5119
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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