Sodium Sulfite → HCID 22316883, compound

HRID 497291Notes

Reaction equation

HRID 497291 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17](SC)=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[CH:22]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:33][S:34]([O-:36])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([S:34]([CH3:22])(=[O:36])=[O:33])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 22316705HCID 22316705, compound

Product 1

HCID 22316883HCID 22316883, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(4-bromophenyl)-2-methyl-4-[4-(methylthio)phenyl]-1,3-thiazole from step 3 (3.8 g, 0.010 mol) in CH2Cl2 (40 mL), m-CPBA (6.2 g, 0.025 mol) was added at 0° C. The mixture was allowed to warm to room temperature and stirred for 12 hours. The mixture was poured into aqueous saturated Na2SO3 (40 mL) and diluted with CH2Cl2 (50 mL). Organic later was separated and washed with aqueous saturated NaHCO3 (50 mL), dried over MgSO4, and concentrated in vacuo. The mixture was purified by flash chromatography eluting with ethyl acetate/hexane (1/1) to give title compound (3.1 g, 76%).

Workup

  1. customOrganic later was separated
  2. washwashed with aqueous saturated NaHCO3 (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe mixture was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-53737608f1084cd789531026321768fc
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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