Hydrochloric Acid → HCID 46219011, compound

HRID 1057218Notes

Reaction equation

HRID 1057218 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[C:5](=[O:30])[CH:6]=[C:7]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:8]2=[O:15].Cl.CN(C)[CH2:34][CH2:35][CH2:36]N=C=NCC.Cl.[Cl-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH:53](Cl)(Cl)Cl>C(O)C(C)C>[CH2:34]([O:28][C:27](=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][S:16][C:7]1[C:8](=[O:15])[C:9]2[C:4]([C:5](=[O:30])[CH:6]=1)=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH:35]([CH3:36])[CH3:53]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6212ChloroformHCID 24436Sodium SulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66664296HCID 66664296, compound

Product 1

HCID 46219011HCID 46219011, compound

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

1.15 mM 11-(5,8-dimethoxy-1,4-dioxo-1,4-dihydronaphthalene-2-ylthio)undecanoic acid (5p) that had been prepared above was dissolved in 60 ml of chloroform in 100 ml one-neck round flask and then, 1.38 mM N-(3-dimethylaminopropyl)-N′-ethylcarbodimide hydro chloride (EDC) and 1.38 mM isobutylalcohol were added thereto and stirred overnight. 1N hydrochloric acid was added to the reaction mixture and stirred at room temperature for 3 minutes. Then, 50 ml of saturated sodium chloride solution was added thereto, followed by extraction three times with 50 ml of chloroform, and obtained organic layers were gathered and dehydrated with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was subjected to silicagel column chromatography, thereby producing isobutyl-11-(5,8-dimethoxy-1,4-dioxo-1,4-dihydronaphthalene-2-ylthio)undecanoate (7a) that was reddish brown. The yield and properties of the synthesized compound are as follows.

Workup

  1. stirringstirred at room temperature for 3 minutes
  2. extractionfollowed by extraction three times with 50 ml of chloroform
  3. customobtained organic layers
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe yield

Sources & evidence

ORD record
ord-45170281053345ecba3262004d5fac9f
Source dataset
uspto-grants-2016_07
Patent number
US09400281B2

Reaction notes

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