Hydrochloric Acid → HCID 178474705, compound

HRID 1493507Notes

Reaction equation

HRID 1493507 reaction equation
[C:1]([CH:4]1[C:9](=[O:10])[CH2:8][CH:7]([CH2:11][CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:6][C:5]1=[O:24])(=O)[CH3:2].Cl.[CH2:26]([O:28][NH2:29])[CH3:27].C(N(CC)CC)C.Cl>C(O)C.O>[CH2:26]([O:28][NH:29][C:1](=[C:4]1[C:5](=[O:24])[CH2:6][CH:7]([CH2:11][CH2:12][S:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=2)[CH2:8][C:9]1=[O:10])[CH3:2])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 143912942-Acetyl-5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dione

Product 1

HCID 178474705HCID 178474705, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.1 Grams of 2-acetyl-5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dione was dissolved in 10 ml of ethanol, and 0.71 g of ethoxyamine hydrochloride and 0.68 g of triethylamine were added to the resulting solution which was then stirred overnight at room temperature. The reaction solution was poured into water, acidified with dilute hydrochloric acid and extracted with chloroform. Chloroform was removed and the residue was purified by column chromatography on silica gel (eluent, ethyl acetate:hexane=1:5) to obtain 1.2 g of 2-(1-ethoxyaminoethylidene)-5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dione as white crystals.

Workup

  1. extractionextracted with chloroform
  2. customChloroform was removed
  3. customthe residue was purified by column chromatography on silica gel (eluent, ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-14a1d1122426445b8009c92fab83070c
Source dataset
uspto-grants-1991_06
Patent number
US05021579

Reaction notes

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