Hydrochloric Acid → HCID 86699517, compound

HRID 571604Notes

Reaction equation

HRID 571604 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16][CH3:17])[C:10]=1[CH2:18][C:19]([N:21]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[N:22]=[C:23]([S:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:24]([O:26]CC)=O)=[O:20])[CH3:8].Cl>C1COCC1>[CH2:7]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16][CH3:17])[C:10]=1[C:18]1[C:19](=[O:20])[N:21]([CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:22]=[C:23]([S:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:24]=1[OH:26])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 68284933HCID 68284933, compound

Product 1

HCID 86699517HCID 86699517, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium t-butoxide (12.4 g, 110 mmol) in dry THF (80 ml) was added a solution of ethyl 2-[2-(2,6-diethyl-4-methylphenyl)acetyl-2-benzylhydrazono]-2-(dodecylthio)acetate (16.4 g, 27.6 mmol) in dry THF (20 ml) dropwise at room temperature over 20 minutes. After being stirred for 10 minutes at room temperature, 1N hydrochloric acid (200 ml) was added, and extracted with tert-butyl methyl ether 2 times. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 1.48 g of Compound (I-12-1) (yield: 13%) as solid and 2.71 g of 4-(2,6-diethyl-4-methylphenyl)-6-dodecylthio-5-hydroxy-2-benzyl-3(2H)-pyridazinone and Compound (I-12-1-B) (yield: 17%) as oil.

Workup

  1. extractionextracted with tert-butyl methyl ether 2 times
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-57e67531231644c5ba8dd61ef0aecd6e
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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