Water → HCID 178474723, compound

HRID 703287Notes

Reaction equation

HRID 703287 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-61738b3cdc704325aa23a25bb076911e
Source dataset
uspto-grants-1991_01
Patent number
US04981971

Reaction notes

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