Sodium Sulfite → HCID 22316883, compound

HRID 396848Notes

Reaction equation

HRID 396848 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 temperrature 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 concentarted 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. temperatureto warm to room temperrature
  2. customOrganic later was separated
  3. washwashed with aqueous saturated NaHCO3 (50 mL)
  4. dry with materialdried over MgSO4
  5. customThe mixture was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-a22fad00c9c94d16bdd22d94ca99fd21
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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