Diethyl Ether → HCID 117702785, compound

HRID 874014Notes

Reaction equation

HRID 874014 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([CH3:10])[CH:3]=1.[F:11][CH:12]([F:16])[C:13](O)=O.CCOCC>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[N:6]([C:13]([CH:12]([F:16])[F:11])=[N:9][N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9788Difluoroacetic acidHCID 114464906-Chloro-3-hydrazinyl-4-methylpyridazine

Product 1

HCID 117702785HCID 117702785, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a beige suspension of 6-chloro-3-hydrazinyl-4-methylpyridazine (step 195.1) (22.44 g, 127 mmol) in dioxane (250 mL) was added difluoroacetic acid (Aldrich) (9.40 mL, 146 mmol) and the reaction mixture was stirred at rt for 5 min, then heated-up to 120° C. for 2.5 hr. With heating the suspension turned into a red-orange solution. The reaction mixture was cooled to rt. Et2O (80 mL) was added and the suspension was stirred for 2 hours at 0° C. Precipitated solids were isolated by filtration, suspended in hexanes and filtered again. After repeated washings with hexanes the tittle compound was obtained as an orange solid.

Workup

  1. temperatureheated-up to 120° C. for 2.5 hr
  2. temperatureWith heating the suspension
  3. temperatureThe reaction mixture was cooled to rt
  4. stirringthe suspension was stirred for 2 hours at 0° C
  5. customPrecipitated solids
  6. customwere isolated by filtration
  7. filtrationfiltered again
  8. washwashings with hexanes the tittle compound
  9. customwas obtained as an orange solid

Sources & evidence

ORD record
ord-0293dee99cc9472abe1e192b8810e005
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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