Hydrochloric Acid → HCID 178454519, compound

HRID 414028Notes

Reaction equation

HRID 414028 reaction equation
[H-].[Na+].Cl.[CH2:4]([O:8][NH2:9])[CH:5]=[CH:6][CH3:7].[C:10]([CH:13]1[C:18](=[O:19])[CH2:17][CH:16]([CH2:20][CH2:21][S:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:15][C:14]1=[O:33])(=O)[CH3:11].Cl>CN(C)C=O.O>[CH2:4]([O:8][NH:9][C:10](=[C:13]1[C:18](=[O:19])[CH2:17][CH:16]([CH2:20][CH2:21][S:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:27][CH:28]=2)[CH2:15][C:14]1=[O:33])[CH3:11])[CH:5]=[CH:6][CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 143912942-Acetyl-5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dioneHCID 71441756O-But-2-en-1-ylhydroxylamine--hydrogen chloride (1/1)

Product 1

HCID 178454519HCID 178454519, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the suspension of 0.3 g of sodium hydride (60% oil dispersion) in 10 ml of dimethylformamide, 0.09 g of 2-butenyloxyamine hydrochloride was added under cooling with ice-water bath and then stirred. After 30 minutes, 0.21 g of 2-acetyl-5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dione was added to the resulting solution which was then stirred for 7 hours under cooling with ice-water bath. The reaction solution was poured into water, acidified with dilute hydrochloric acid and extracted with ether. After removing ether, the residue was purified by thin layer chromatography (eluent, hexane:ethyl acetate=5:1) to obtain 0.22 g of 2-[1-(2-butenyloxyamino)ethylidene]5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dione.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice-water bath
  3. stirringwas then stirred for 7 hours
  4. temperatureunder cooling with ice-water bath
  5. extractionextracted with ether
  6. customAfter removing ether
  7. customthe residue was purified by thin layer chromatography (eluent, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-4baad5d64f9340a894e93c3bf3c345cd
Source dataset
uspto-grants-1988_12
Patent number
US04789396

Reaction notes

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