Potassium Carbonate → HCID 137231112, compound

HRID 2174175Notes

Reaction equation

HRID 2174175 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([C:12](=O)[CH3:13])=[N:9][N:8]=2)[CH:2]=1.Cl.[NH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([C:12](=[N:16][OH:17])[CH3:13])=[N:9][N:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 58416009HCID 58416009, compound

Product 1

HCID 137231112HCID 137231112, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]ethanone (1.0 g, 4.68 mmol, prepared according to WO 2010/006713) in 50 ml EtOH was treated with hydroxylamine hydrochloride (0.345 g, 4.91 mmol) and potassium carbonate (0.686 g, 4.91 mmol), and stirred at room temperature, monitored by LCMS and TLC. After 3 hours, the mixture was concentrated in vacuo to approximately 10 ml. Addition of saturated ammonium chloride gave a precipitate which was filtered, and washed successively with water, isopropanol, and tertiary-butyl methyl ether. This yielded 1-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]ethanone oxime (577 mg, 51%) as a 5:1 mixture of isomers.

Workup

  1. concentrationthe mixture was concentrated in vacuo to approximately 10 ml
  2. additionAddition of saturated ammonium chloride
  3. customgave a precipitate which
  4. filtrationwas filtered
  5. washwashed successively with water, isopropanol, and tertiary-butyl methyl ether
  6. additionThis yielded 1-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]ethanone oxime (577 mg, 51%) as a 5:1 mixture of isomers

Sources & evidence

ORD record
ord-ff3015451bc440b1b06b8cf29e7ed897
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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