Stearic Acid → HCID 13146241, compound

HRID 2413214Notes

Reaction equation

HRID 2413214 reaction equation
[C:1]([OH:20])(=[O:19])[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][CH2:15][CH2:16][CH2:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:36][S:37]([O:40][C:41]1[CH:50]=[CH:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:51](=[NH:53])[NH2:52])[CH:47]=2)[CH:42]=1)(=[O:39])=[O:38]>N1C=CC=CC=1>[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].[C:1]([O:20][C:41]1[CH:50]=[CH:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:51](=[NH:52])[NH2:53])[CH:47]=2)[CH:42]=1)(=[O:19])[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][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 5281Stearic AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146241HCID 13146241, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5.0 g of stearic acid in 70 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 successively with a small volume of pyridine, ethyl ether, and acetone, dissolved in a dimethylformamide-methanol mixture, and filtered to remove the insolubles. The crystals formed upon addition of ethyl ether to the filtrate were collected by filtration, washed with ethanol, and recrystallized from a dimethylformamide-methanol mixture to obtain 3.3 g of a white to pale brown powder of 6-amidino-2-naphthyl stearate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed successively with a small volume of pyridine, ethyl ether, and acetone
  4. dissolutiondissolved in a dimethylformamide-methanol mixture
  5. filtrationfiltered
  6. customto remove the insolubles
  7. customThe crystals formed upon addition of ethyl ether to the filtrate
  8. filtrationwere collected by filtration
  9. washwashed with ethanol
  10. customrecrystallized from a dimethylformamide-methanol mixture

Sources & evidence

ORD record
ord-3fc0e94f79d94206b1e0e75b5bafd8b0
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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