Potassium Carbonate → HCID 131732977, compound

HRID 2174179Notes

Reaction equation

HRID 2174179 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:12](=O)[CH3:13])=[CH:10][N:11]=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:8][C:9]([C:12](=[N:16][OH:17])[CH3:13])=[CH:10][N:11]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 1481569HCID 1481569, compound

Product 1

HCID 131732977HCID 131732977, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-[2-(3-pyridyl)thiazol-5-yl]ethanone (0.8 g, 3.76 mmol) in 50 ml EtOH was treated with hydroxylamine hydrochloride (0.277 g, 3.95 mmol) and potassium carbonate (0.551 g, 3.95 mmol), and stirred at ambient temperature, monitored by LCMS and TLC, which indicated a ca. 1:1 mixture of isomer formation. After 3 hours, the mixture was concentrated in vacuo to approximately 10 ml. Addition of saturated ammonium chloride gave Isomer A of the title product as a beige precipitate which was filtered, and washed successively with water, isopropanol, and tertiary-butyl methyl ether (yield 156 mg).

Workup

  1. additiona ca. 1:1 mixture of isomer formation
  2. concentrationthe mixture was concentrated in vacuo to approximately 10 ml
  3. additionAddition of saturated ammonium chloride

Sources & evidence

ORD record
ord-8e9f61d9d3114de092902453351034fd
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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