Ethanol → 4-Methoxyimino-5-methyl-6-bromothiochroman

HRID 1292503Notes

Reaction equation

HRID 1292503 reaction equation
[CH3:1][C:2]1[C:11]([Br:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=O)[CH2:5][CH2:6][S:7]2.Cl.[CH3:15][O:16][NH2:17].C(O)C>N1C=CC=CC=1>[CH3:15][O:16][N:17]=[C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[C:11]([Br:12])[C:2]=2[CH3:1])[S:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 152784785-Methyl-6-bromothiochroman-4-one

Product 1

HCID 543825024-Methoxyimino-5-methyl-6-bromothiochromanYield 93.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.0 Grams (12 mmol) of 5-methyl-6-bromothiochroman-4-one and 1.9 g (23 mmol) of O-methylhydroxylamine hydrochloride were refluxed in a solvent mixture of 10 ml of ethanol and 10 ml of pyridine under heat for 30 minutes. The solvents were distilled off under reduced pressure, 50 ml of 5% hydrochloric acid was added, and a formed solid was recovered by filtration, washed with water and then dried to give 3.2 g (yield 93%) of 4-methoxyimino-5-methyl-6-bromothiochroman.

Workup

  1. temperatureunder heat for 30 minutes
  2. distillationThe solvents were distilled off under reduced pressure, 50 ml of 5% hydrochloric acid
  3. additionwas added
  4. filtrationa formed solid was recovered by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4dba90d7e68d47ed91d36ebde12d2606
Source dataset
uspto-grants-1998_05
Patent number
US05756759

Reaction notes

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