Sodium Carbonate → HCID 22909641, compound

HRID 1379092Notes

Reaction equation

HRID 1379092 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[S:16][C:17]1[O:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:20][N:21]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:36])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.ClCl>[C:12]([C:7]1[CH:8]=[C:9]([OH:11])[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]=1[S:16]([C:17]1[O:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:20][N:21]=1)=[O:36])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22909643HCID 22909643, compound

Product 1

HCID 22909641HCID 22909641, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

To a solution of 2-(2,6-ditertbutyl-4-hydroxyphenyl)thio-5-(2-pyridyl)-1,3,4-oxadiazole (1.25 g, 0.00325 mol) in CH2Cl2 (30 ml) at rt was added dropwise a solution of mCPBA (1.04 g, 0.0039 mol, 65% pure) in CH2 Cl2 (25 ml) over 30 min. The reaction was stirred at rt for an additional 1.5 h and treated with sat aq. Na2S2O3 (5 ml) and sat. aq. Na2CO3 (20 ml). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×25 ml), dried (MgSO4) and the solvent evaporated in vacuo. Chromatography on silica gel using ethyl acetate/hexanes (1/1) as the eluant gave 2-(2,6-di-tertbutyl-4-hydroxyphenyl)sulfinyl-5-(2-pyridyl)-1,3,4-oxadiazole (98) as a white solid (0.900 g, 70%); m.p. 172.5°-173.0° C.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×25 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c780489ce4e34129bb32144d640087da
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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