Hydroxyamine hydrochloride → HCID 73708224, compound

HRID 2296358Notes

Reaction equation

HRID 2296358 reaction equation
[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH3:10])[C:6]1=O)([O:3][CH3:4])=[O:2].Cl.[NH2:13][OH:14]>N1C=CC=CC=1>[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH3:10])[C:6]1=[N:13][OH:14])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 126586981,4-Anhydro-2,5-dideoxy-2-(methoxycarbonyl)-1-thiopent-3-ulose

Product 1

HCID 73708224HCID 73708224, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 37.26 g. (0.214 mole) of 4-carbomethoxy-3-keto-2-methyltetrahydrothiophene in 100 ml. anhydrous pyridine was treated with 18.0 g. (0.261 mole) hydroxylamine hydrochloride. The mixture was stirred 24 hours at 25°. The reaction was concentrated and partitioned between 1 N hydrochloric acid/methylene chloride. The aqueous phase was extracted two times with methylene chloride. The combined organic extracts were dried and evaporated to yield 40.1 g (99%) of pure 4-carbomethoxy-3-keto-2-methyltetrahydrothiophene oxime as a colorless oil.

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between 1 N hydrochloric acid/methylene chloride
  3. extractionThe aqueous phase was extracted two times with methylene chloride
  4. customThe combined organic extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-6404d9a14502427f936b8ad0b3ccc9e9
Source dataset
uspto-grants-1984_01
Patent number
US04428963

Reaction notes

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