Sulfuric Acid → HCID 67377775, compound

HRID 877481Notes

Reaction equation

HRID 877481 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH:10]N=C1CCCCC1=O.OS(O)(=O)=O.[C:24]([O-:27])(O)=O.[Na+]>CC#N>[Cl:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([Cl:1])=[C:3]2[C:4]=1[C:2]1[CH2:3][CH2:4][CH2:5][C:24](=[O:27])[C:7]=1[NH:10]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86676826HCID 86676826, compound

Product 1

HCID 67377775HCID 67377775, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-(2,4,5-Trichlorophenyl)hydrazono)cyclohexanone (0.3 g, 0.98 mmol) was dissolved in MeCN (6 mL) and H2SO4 (0.1 mL, 1.8 M solution) was added. The reaction mixture was heated to 80° C. for 4 h and slowly cooled to room temperature. Saturated NaHCO3 was added to the reaction mixture until pH 5-6 was obtained and then extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to obtain the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant] to furnish the title compound as a brown solid (0.1 g, 35%). 1H NMR (200 MHz, DMSO-d6, δ in ppm) 12.55 (bs, 1H), 7.68 (s, 1H), 3.27 (t, J=5.6 Hz, 2H), 2.63 (t, J=6.0 Hz, 2H), 2.19 (m, 2H).

Workup

  1. temperatureslowly cooled to room temperature
  2. customwas obtained
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto obtain the crude compound which
  7. customwas purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant]

Sources & evidence

ORD record
ord-5fc72a2aace04b0da2731946918f881b
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

Loading…