Hydrochloric Acid → HCID 86754603, compound

HRID 1739383Notes

Reaction equation

HRID 1739383 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[S:12][CH2:11][N:10]([CH3:13])[CH:9]=1)[O:6][CH3:7])=O.Cl.[NH2:19][OH:20].N1C=CC=CC=1.Cl>CO>[OH:20][N:19]=[CH:1][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[S:12][CH2:11][N:10]([CH3:13])[CH:9]=1)[O:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 21840896HCID 21840896, compound

Product 1

HCID 86754603HCID 86754603, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.39 g (6 mmol) of 5-(2-formyl-α-methoxybenzyl)-3-methylthiazole in 12 ml of methanol was added 0.83 g (12 mmol) of hydroxylamine hydrochloride and 1.07 ml (13.2 mmol) of pyridine and stirred under reflux for 2 hours. After completion of the reaction, 200 ml of 0.1N hydrochloric acid was added and extracted twice with 100 ml of dichloromethane. The dichloromethane layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 5-(2-hydroxyiminomethyl-α-methoxybenzyl)-3-methylthiazole (1.20 g, 81.2%) as oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionwas added
  3. extractionextracted twice with 100 ml of dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-70c27c85054c46809d96362bbcdf9d7a
Source dataset
uspto-grants-1999_10
Patent number
US05965740

Reaction notes

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