Hydrochloric Acid → HCID 178418678、化合物

HRID 5262

反応式

HRID 5262 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 178418678HCID 178418678、化合物収率 30%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07070efa6bb7493ba824bd6a67d62928
出典データセット
uspto-grants-1993_09
特許番号
US05242945

関連ノート

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