Decanoic Acid → HCID 13146234, compound

HRID 2413211Notes

Reaction equation

HRID 2413211 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:3].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:45])[NH2:44])[CH:39]=2)[CH:34]=1)(=O)=O>N1C=CC=CC=1>[O:3]([C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:44])[NH2:45])[CH:39]=2)[CH:34]=1)[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:1]

Participants

5

Reactant 3

HCID 2969Decanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146234HCID 13146234, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.0 g of capric 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 separated by filtration and washed with a small volume of pyridine. The filtrate and washings were poured into stirred ethyl ether. The precipitated crystals were collected by filtration, washed with ethyl ether, then with acetone, and recrystallized from a methanol-ether mixture to yield 1.2 g of a white powder of 6-amidino-2-naphthyl caprate methanesulfonate.

Workup

  1. stirringfurther stirred overnight at room temperature
  2. customThe precipitate was separated by filtration
  3. washwashed with a small volume of pyridine
  4. additionThe filtrate and washings were poured
  5. stirringinto stirred ethyl ether
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with ethyl ether
  8. customwith acetone, and recrystallized from a methanol-ether mixture

Sources & evidence

ORD record
ord-c2e57cc08244401babbf7508857ac327
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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