Sodium Hydroxide → HCID 23317187, compound

HRID 1982127Notes

Reaction equation

HRID 1982127 reaction equation
P(Br)(Br)([Br:3])=O.[CH2:6]([C:11]1[CH:12]=[CH:13][C:14](=O)[NH:15][N:16]=1)[CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[Br:3][C:14]1[N:15]=[N:16][C:11]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 23317181HCID 23317181, compound

Product 1

HCID 23317187HCID 23317187, compoundYield 144%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
65 °C

Procedure

A solution of 18.6 g of phosphorus oxybromide in 18.6 g of absolute toluene was diluted with 100 ml of absolute toluene in a sulphonation flask under nitrogen, heated to 65° C. and treated dropwise within 1.5 hours with a solution of 21.6 g of 6-pentyl-3(2H)-pyridazinone (prepared according to Example 3) in 100 ml of absolute toluene. A grey coloured difficultly stirrable suspension formed occasionally. For the completion of the reaction, the mixture was stirred at 65° C. overnight (18 hours), then cooled to room temperature, poured into 250 ml of water and stirred well. The aqueous phase was neutralized with 28% (wt./vol.) sodium hydroxide solution and with sodium hydrogen carbonate. The organic phase was separated and the aqueous phase was back-extracted with 100 ml of tert.butyl methyl ether. The combined organic phases were washed with 100 ml of water, dried over sodium sulphate and evaporated on a rotary evaporator. The brown coloured crude product was subsequently distilled in a high vacuum, there being obtained 21.4 g (72%) of 3-bromo-6-pentylpyridazine in the form of a brown oil (b.p. 99°-108° C./0.04-0.06 Torr) which crystallized upon cooling. Recrystallization of a sample from methyl formate at -20° C. gave white crystals of melting point 31°-32° C.

Workup

  1. customformed occasionally
  2. customFor the completion of the reaction
  3. temperaturecooled to room temperature
  4. stirringstirred well
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was back-extracted with 100 ml of tert.butyl methyl ether
  7. washThe combined organic phases were washed with 100 ml of water
  8. dry with materialdried over sodium sulphate
  9. customevaporated on a rotary evaporator
  10. distillationThe brown coloured crude product was subsequently distilled in a high vacuum

Sources & evidence

ORD record
ord-b690228f813a416db4930166e2839162
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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