Hydrochloric Acid → HCID 178454519, compound

HRID 1493512Notes

Reaction equation

HRID 1493512 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-aaa493d4aaea4e2186a3ac2a17dfb83d
Source dataset
uspto-grants-1991_06
Patent number
US05021579

Reaction notes

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