Trifluoroacetic acid → HCID 178526776, compound

HRID 1637619Notes

Reaction equation

HRID 1637619 reaction equation
[N+:1]([C:4]1[N:8]2[N:9]=[C:10]([S:13]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=[CH:12][C:7]2=[N:6][CH:5]=1)([O-:3])=[O:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[N+:1]([C:4]1[N:8]2[N:9]=[C:10]([SH:13])[CH:11]=[CH:12][C:7]2=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 187994273-Nitro-6-tritylsulfanylimidazo[1,2-b]pyridazine

Product 1

HCID 178526776HCID 178526776, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (2.28 mmol) of 3-nitro-6-tritylsulfanylimidazo[1,2-b]pyridazine in 10 ml of anhydrous dichloromethane is treated with 0.73 ml (4.56 mmol) of triethylsilane and 1.0 ml (13 mmol) of trifluoroacetic acid under an argon atmosphere and stirred at room temperature for 3 h. 10 ml of 2N sodium hydroxide solution is then added and the mixture is extracted with 3×20 ml of ethyl acetate. The aqueous phase is then adjusted to pH 2 using hydrochloric acid and subsequently extracted with 3×20 ml of ethyl acetate. The organic extracts are washed with 20 ml of water, dried over magnesium sulfate and concentrated. The residue is crystallized by addition of a little diethyl ether. 0.34 g (76%) of the title compound is isolated as a pale yellow solid. M.p. 175-177° C.

Workup

  1. extractionthe mixture is extracted with 3×20 ml of ethyl acetate
  2. extractionsubsequently extracted with 3×20 ml of ethyl acetate
  3. washThe organic extracts are washed with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized by addition of a little diethyl ether

Sources & evidence

ORD record
ord-0d9d0afc38254cbc85498b6742422370
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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