P-Cresol → HCID 9881592, compound

HRID 1586005Notes

Reaction equation

HRID 1586005 reaction equation
[Na].Cl[C:3]1[N:4]=[N:5][C:6]([S:9][CH2:10][CH:11]=[CH2:12])=[CH:7][CH:8]=1.[CH:13]1[C:18]([OH:19])=[CH:17][CH:16]=[C:15]([CH3:20])[CH:14]=1>>[CH3:20][C:15]1[CH:14]=[CH:13][C:18]([O:19][C:3]2[N:4]=[N:5][C:6]([S:9][CH2:10][CH:11]=[CH2:12])=[CH:7][CH:8]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 2879P-CresolHCID 5360545SodiumHCID 212176673-Chloro-6-[(prop-2-en-1-yl)sulfanyl]pyridazine

Product 1

HCID 9881592HCID 9881592, compound

Conditions

Temperature
100 °C

Procedure

0.23 g(0.01 mol) of metallic sodium was dissolved in 30 ml of dry p-cresol. To the resulting solution was added 1.87 g(0.01 mol) of 3-chloro-6-allylthiopyridazine and then the reaction solution was stirred for 5 hours at 100±5° C. After the reaction was allowed to stop, the reaction solution was cooled and adjusted to alkaline (pH 14) with 150 ml of 2N--NaOH, thereby precipitating the crystals. The precipitated crystal was extracted with diethyl ether, washed twice with purified water, dried over anhydrous magnesium sulfate and then concentrated to remove diethyl ether. The resulting oily residue was slowly cooled to obtain the title compound as a pale white amorphous crystal.

Workup

  1. temperaturethe reaction solution was cooled
  2. customNaOH, thereby precipitating the crystals
  3. extractionThe precipitated crystal was extracted with diethyl ether
  4. washwashed twice with purified water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto remove diethyl ether
  8. temperatureThe resulting oily residue was slowly cooled

Sources & evidence

ORD record
ord-7571f0ff64d54e3695bb6bbff0bcc8a2
Source dataset
uspto-grants-1999_08
Patent number
US05942511

Reaction notes

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