Phosphorus oxychloride → HCID 178445606, compound

HRID 1982114Notes

Reaction equation

HRID 1982114 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16](=O)[NH:17][N:18]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:16]1[N:17]=[N:18][C:13]([CH2:12][CH2:11][C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178445607HCID 178445607, compound

Product 1

HCID 178445606HCID 178445606, compound

Conditions

Temperature
0 °C

Procedure

21.0 g of 6-[2-(trans-4-butylcyclohexyl)ethyl]-3(2H)-pyridazinone are treated with 20 ml of phosphorus oxychloride and slowly heated to reflux. After boiling under reflux for 20 minutes, the excess phosphorus oxychloride is distilled off. The residue is cooled 0° C., hydrolyzed cautiously with 100 g of crushed ice, then neutralized with sodium hydrogen carbonate and extracted three times with 100 ml of tert.butyl methyl ether each time. The combined organic phases are dried over sodium sulphate and freed from solvent on a rotary evaporator. The crude product of 3-chloro-6-[2-(trans-4-butylcyclohexyl)ethyl]pyridazine obtained is recrystallized from ethanol.

Workup

  1. temperatureslowly heated to reflux
  2. temperatureunder reflux for 20 minutes
  3. distillationthe excess phosphorus oxychloride is distilled off
  4. extractionextracted three times with 100 ml of tert.butyl methyl ether each time
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customfreed from solvent on a rotary evaporator

Sources & evidence

ORD record
ord-ee3c74a0372d438cb28fe49390a5cd90
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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