Hexane → 3,6-Bis(diphenylphosphinyl)pyridazine

HRID 1065631

Reaction equation

HRID 1065631 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]1([P:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:16]C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>ClC1C=CC=CC=1Cl>[C:9]1([P:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:2]2[N:3]=[N:4][C:5]([P:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:26]3[CH:25]=[CH:24][CH:29]=[CH:28][CH:27]=3)=[O:16])=[CH:6][CH:7]=2)=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 673313,6-DichloropyridazineHCID 77636Methoxydiphenylphosphine

Product 1

HCID 205394883,6-Bis(diphenylphosphinyl)pyridazine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirred, refluxing solution of 3.00 g of 3,6-dichloropyridazine in 50 ml of o-dichlorobenzene under nitrogen was added dropwise 10.00 g of methyl diphenylphosphinite. After the addition was completed, the mixture was refluxed for 7 hours and then cooled. The cooled mixture was mixed with excess hexane; the oil which formed slowly crystallized. The resultant solid was separated by filtration, washed with hexane, and recrystallized twice from ethanol with decolorizing charcoal treatment to give 0.93 g of 3,6-bis(diphenylphosphinyl)pyridazine (shown by formula in claim 7) as slightly off-white crystals, mp 248°-251.5° C. Anal. Calcd for C28H22N2O2P2 : C, 70.00; H, 4.62; N, 5.83; P, 12.89. Found: C, 69.72; H, 4.92; N, 5.78; P, 12.82.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 7 hours
  3. temperaturecooled
  4. customthe oil which formed slowly
  5. customcrystallized
  6. customThe resultant solid was separated by filtration
  7. washwashed with hexane
  8. customrecrystallized twice from ethanol with decolorizing charcoal treatment

Sources & evidence

ORD record
ord-511b63dc2056448fbe0e45e1d96a37b5
Source dataset
uspto-grants-1982_05
Patent number
US04330461

Linked notes

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