Dichloromethane → HCID 24864282, compound

HRID 1392870Notes

Reaction equation

HRID 1392870 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)=[C:8]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[F-:36].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:12][F:36])=[C:8]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 86600393HCID 86600393, compound

Product 1

HCID 24864282HCID 24864282, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 15 ml round bottom flask charged with 2-tert-butyl-4-p-toluenesulfonyloxymethyl-5-(4-tert-butylbenzyl)thio-3(2H)-pyridazinone (0.5 g, 0.972 mmol) is added 4.86 ml of tetrabutylammonium fluoride solution (1M in THF, 4.86 mmol). The mixture is first stirred at room temperature for 15 minutes after which it is heated for 15 minutes at 100° C. The solution is then cooled to room temperature and to it is added dichloromethane followed by water. The layers were separated and the organic layer is washed with water and then dried. The organic layer is then concentrated and subjected to purification using silica gel flash chromatography (ethyl acetate/hexanes) to obtain the above compound.

Workup

  1. temperatureis heated for 15 minutes at 100° C
  2. temperatureThe solution is then cooled to room temperature and to it
  3. customThe layers were separated
  4. washthe organic layer is washed with water
  5. customdried
  6. concentrationThe organic layer is then concentrated
  7. customsubjected to purification
  8. customto obtain the above compound

Sources & evidence

ORD record
ord-69751cbfbe0541d5a5e775fdf5fdde28
Source dataset
uspto-grants-2008_03
Patent number
US07344702B2

Reaction notes

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