Hexachloroethane → HCID 57472626, compound

HRID 501405Notes

Reaction equation

HRID 501405 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][N:12]1[C:17](=[O:18])[C:16]2[N:19]=[CH:20][N:21]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15]=2[CH:14]=[N:13]1.[Cl:41]C(Cl)(Cl)C(Cl)(Cl)Cl.[Cl-].[NH4+]>O1CCCC1>[Cl:41][C:20]1[N:21]([C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:15]2[CH:14]=[N:13][N:12]([CH3:11])[C:17](=[O:18])[C:16]=2[N:19]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 57472624HCID 57472624, compound

Product 1

HCID 57472626HCID 57472626, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

220 ml of lithium hexamethyldisilazide (1.0 M tetrahydrofuran solution) was added to a 4-L tetrahydrofuran solution of 68.3 g of 5-methyl-1-trityl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one at −75° C. under a nitrogen atmosphere, and the mixture was stirred at −75° C. for 1 hour. Then, 200 ml of a tetrahydrofuran solution of 82.3 g of hexachloroethane was added to the solution. The mixture was allowed to warm to −20° C. 5 L of 5% aqueous ammonium chloride was added, and the mixture was extracted with 4 L of ethyl acetate. The organic layer was washed successively with 5 L of water and 5 L of a saturated sodium chloride solution. The solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was suspended in 150 ml of t-butyl methyl ether, and then collected by filtration. The solid was washed twice with 100 ml of t-butyl methyl ether to give 69.7 g of the title compound.

Workup

  1. temperatureto warm to −20° C
  2. extractionthe mixture was extracted with 4 L of ethyl acetate
  3. washThe organic layer was washed successively with 5 L of water and 5 L of a saturated sodium chloride solution
  4. dry with materialThe solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationcollected by filtration
  7. washThe solid was washed twice with 100 ml of t-butyl methyl ether

Sources & evidence

ORD record
ord-ece8b764c29e4d65971347a3b9c430f8
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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