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Hydrochloric Acid → HCID 178418678, compound

HRID 5262
Notes
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Reaction equation

HRID 5262 reaction equation
[CH2:1]1[C:6](=[O:7])[S:5][CH2:4][C:2]1=[O:3].Cl.CN(C)CCCN=C=NCC.[C:20](O)(=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].Cl>CN(C)C=O.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[OH:3][C:2]1[CH2:4][S:5][C:6](=[O:7])[C:1]=1[C:20](=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5280450Linoleic AcidHCID 10214383Thiotetronic acid

Product 1

HCID 178418678HCID 178418678, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8471TriethylamineSolvent

Procedure

To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 ML (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-dimethylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4.96 g (17.7 mmol) of linoleic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is recrystallized from pentane at -78° C. to give a solid which melts upon warming to room temperature giving 1.67 g (30%) of 4-hydroxy-3-[(Z,Z)-1-oxo-9,12-octadecadienyl]-2(5H)-thiophenone as an oil.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallized from pentane at -78° C.
  7. customto give a solid which
  8. temperatureupon warming to room temperature

Sources & evidence

ORD record
ord-07070efa6bb7493ba824bd6a67d62928
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05242945

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes