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

HRID 129569Notes

Reaction equation

HRID 129569 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.[CH3:16][O:17][NH2:18].C(O)C>N1C=CC=CC=1>[CH3:16][O:17][N:18]=[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

Participants

5

Reactant 3

HCID 702EthanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 152784955,8-Dimethyl-6-bromothiochroman-4-one

Product 1

HCID 541313624-Methoxyimino-5,8-dimethyl-6-bromothiochromanYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.2 Grams (12 mmol) of 5,8-dimethyl-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 solvent was 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 3.4 g of 4-methoxyimino-5,8-dimethyl-6-bromothiochroman (yield 93%).

Workup

  1. temperatureunder heat for 30 minutes
  2. distillationThe solvent was 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-892f1fff2abc43fe8a979baa42bc9b8e
Source dataset
uspto-grants-1995_11
Patent number
US05468878

Reaction notes

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