Water → HCID 178474723, compound

HRID 1493510Notes

Reaction equation

HRID 1493510 reaction equation
[C:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH2:12][CH:13]([S:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[CH3:14])[CH2:7][C:6]1=[O:26])(=O)[CH2:2][CH3:3].Cl.[CH2:28]([O:30][NH2:31])[CH3:29].C(N(CC)C1C=CC=CC=1)C.O>C(OCC)(=O)C>[CH2:28]([O:30][NH:31][C:1](=[C:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH2:12][CH:13]([S:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][CH:17]=2)[CH3:14])[CH2:7][C:6]1=[O:26])[CH2:2][CH3:3])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7061N,N-DiethylanilineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 15017465HCID 15017465, compound

Product 1

HCID 178474723HCID 178474723, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.27 Gram of 2-propionyl-5-[2-(4-trifluoromethylphenylthio)propyl]cyclohexane-1,3-dione was dissolved in 10 ml of ethyl acetate, and 0.08 g of ethoxyamine hydrochloride and 0.1 g of N,N-diethylaniline were added to the resulting solution which was then refluxed for 5 hours. The reaction solution was cooled to room temperature, poured into water, weakly acidified and extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid and water subsequently and dried over anhydrous magnsium sulfate. After removing ethyl acetate, the residue was purified by thin layer chromatography (eluent, hexane:ethyl acetate=5:1) to obtain 0.13 g of 2-(1-ethoxyaminopropylidene)-5-[2-(4-trifluoromethylphenylthio)propyl]cyclohexane-1,3-dione.

Workup

  1. temperaturewas then refluxed for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with dilute hydrochloric acid and water subsequently
  4. dry with materialdried over anhydrous magnsium sulfate
  5. customAfter removing ethyl acetate
  6. customthe residue was purified by thin layer chromatography (eluent, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e1f9e929edfb4802a3ee165031b65338
Source dataset
uspto-grants-1991_06
Patent number
US05021579

Reaction notes

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