Ethanol → 4-Ethoxyimino-5,8-dimethyl-6-bromothiochroman

HRID 233125Notes

Reaction equation

HRID 233125 reaction equation
[CH3:1][C:2]1[C:11]([Br:12])=[CH:10][C:9]([CH3:13])=[C:8]2[C:3]=1[C:4](=O)[CH2:5][CH2:6][S:7]2.Cl.[CH2:16]([O:18][NH2:19])[CH3:17].C(O)C>N1C=CC=CC=1>[CH2:16]([O:18][N:19]=[C:4]1[C:3]2[C:8](=[C:9]([CH3:13])[CH:10]=[C:11]([Br:12])[C:2]=2[CH3:1])[S:7][CH2:6][CH2:5]1)[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 76850O-ethylhydroxylamine hydrochlorideHCID 152784955,8-Dimethyl-6-bromothiochroman-4-one

Product 1

HCID 536838844-Ethoxyimino-5,8-dimethyl-6-bromothiochromanYield 92.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.0 Grams (11 mmol) of 5,8-dimethyl-6-bromothiochroman-4-one and 2.2 g (22 mmol) of O-ethylhydroxylamine hydrochloride were refluxed under heat in a mixed solvent containing 10 ml of ethanol and 10 ml of pyridine for 30 minutes. The solvents were distilled off under reduced pressure, and then the residue was treated with 5% hydrochloric acid and extracted with ethyl acetate. The so-obtained solution was consecutively washed with 5% aqueous potassium carbonate and with saturated sodium chloride solution and dried over sodium sulfate. The solvent was distilled off to give 3.2 g of 4-ethoxyimino-5,8-dimethyl-6-bromothiochroman (yield 92%).

Workup

  1. temperatureunder heat in a mixed solvent
  2. distillationThe solvents were distilled off under reduced pressure
  3. additionthe residue was treated with 5% hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe so-obtained solution was consecutively washed with 5% aqueous potassium carbonate and with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-496dffede0274060be8dff7ae75c5eac
Source dataset
uspto-grants-1997_01
Patent number
US05591868

Reaction notes

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