Potassium Carbonate → HCID 53792155, compound

HRID 1613561Notes

Reaction equation

HRID 1613561 reaction equation
[C:1]1([S:7][CH2:8][C:9]2([CH:12]([CH3:15])[CH:13]=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.C(=O)([O-])[O-].[K+].[K+]>C(O)COCCO>[C:1]1([S:7][CH2:8][C:9]2([CH:12]([CH3:15])[CH3:13])[CH2:10][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 19774070HCID 19774070, compound

Product 1

HCID 53792155HCID 53792155, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 14 (2.12 g, 8.62 mmol), hydrazine hydrate (55% in water, 7.4 mL, 131 mmol) and potassium carbonate (3.2 g, 23.2 mmol) in diethylene glycol (21 mL) was heated at 150° C. (bath temperature) for 3 hr. After cooled to ambient temperature, the mixture was poured into ice water and extracted with n-hexane. The combined organic layers were washed with cold diluted hydrochloric acid, water, sodium bicarbonate solution and brine, and dried over sodium sulfate. Filtration and concentration gave 1.81 g of an oily material, which was purified by column chromatography (silica gel 20 g, 1-2% ethyl acetate in n-hexane) to give 1.69 g (85.1%) of 15, as a colorless oil.

Workup

  1. temperatureAfter cooled to ambient temperature
  2. extractionextracted with n-hexane
  3. washThe combined organic layers were washed with cold diluted hydrochloric acid, water, sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-b709c996e179409abda437188764e524
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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