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

HRID 1720226Notes

Reaction equation

HRID 1720226 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 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 50 ml of 5% hydrochloric acid was added to form a solid. The solid was recovered by filtration, washed with water and dried to give 3.2 g of 4-methoxyimino-5-methyl-6-bromothiochroman (yield 93%).

Workup

  1. temperatureunder heat in a mixed solvent
  2. distillationThe solvents were distilled off under reduced pressure
  3. addition50 ml of 5% hydrochloric acid was added
  4. customto form a solid
  5. filtrationThe solid was recovered by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9707e2c04a0a4593be6eb37c088f2cde
Source dataset
uspto-grants-1996_04
Patent number
US05506194

Reaction notes

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