Sodium Sulfite → HCID 10172306, compound

HRID 895131Notes

Reaction equation

HRID 895131 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]([CH2:15][C:16]1[N:17]=[N:18][N:19]([C:21]2[CH:26]=[C:25]([F:27])[C:24]([N:28]3[CH2:33][CH2:32][S:31][CH2:30][CH2:29]3)=[C:23]([F:34])[CH:22]=2)[CH:20]=1)=[N+:13]=[N-:14].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[N:12]([CH2:15][C:16]1[N:17]=[N:18][N:19]([C:21]2[CH:26]=[C:25]([F:27])[C:24]([N:28]3[CH2:33][CH2:32][S:31](=[O:6])[CH2:30][CH2:29]3)=[C:23]([F:34])[CH:22]=2)[CH:20]=1)=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 10308758HCID 10308758, compound

Product 1

HCID 10172306HCID 10172306, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperoxybenzoic acid (75%, 545 mg, 2.36 mmol) was added to a solution of 4-[4-(4-azidomethyl-[1,2,3]triazol-1-yl)-2,6-difluoro-phenyl]-thiomorpholine (800 mg mmol), obtained in Example 13, in dichloromethane (10 mL) at 0° C. and allowed to stir for 1 h. The reaction mixture was then diluted with dichloromethane (20 mL) and a solution of sodium sulfite was added. Aqueous layer was separated and the dichloromethane layer was washed with water followed by brine and dried over sodium sulfate. Removal of volatiles produced the title sulfoxide (800 mg, 95%).

Workup

  1. customAqueous layer was separated
  2. washthe dichloromethane layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customRemoval of volatiles

Sources & evidence

ORD record
ord-2f6de097f3d3469dbb9794d3ca0b2920
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

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