Sodium Sulfite → HCID 86691022, compound

HRID 1191952Notes

Reaction equation

HRID 1191952 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][N:11]=2)=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O.[O-]S([O-])=O.[Na+].[Na+]>C(#N)C>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]([Br:18])=[CH:10][N:11]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 57258430HCID 57258430, compound

Product 1

HCID 86691022HCID 86691022, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-(biphenyl-4-yl)thiazole (540 mg, 2.28 mmol) in anhydrous acetonitrile (10 mL) was added a solution of N-bromosuccinimide in anhydrous acetonitrile (10 mL). The reaction was stirred for 20 h at room temperature. Subsequently, an aqueous solution of Na2SO3 10% (10 ml) was added and the mixture was stirred for 10 minutes. Then, extracted with ethyl acetate (4×25 mL) and the organic layers were washed with an aqueous saturated solution of NaCl (4×50 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. Flash chromatography of the residue on silica gel (SiO2, hexane:ethyl acetate, 9:1) afforded 500 mg of 2-(biphenyl-4-yl)-5-bromothiazole as a white solid (69% yield). EM (IE): m/z (%): 317; (M+, 100), 315; (M+, 95), 316; (M+, 17.1). HRMS (ESI): (M+H)+: calculated for C15H10BrNS: 315.9717. found: 315.9786.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionThen, extracted with ethyl acetate (4×25 mL)
  3. washthe organic layers were washed with an aqueous saturated solution of NaCl (4×50 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e0318a00ea0b4e4b9ee8f9593c140831
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

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