Chlorotrimethylsilane → 2-(4-Bromophenyl)benzothiazole

HRID 2041822Notes

Reaction equation

HRID 2041822 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18].C[Si](Cl)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 87132-AminothiophenolHCID 685154-Bromobenzoyl chloride

Product 1

HCID 23206022-(4-Bromophenyl)benzothiazoleYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromobenzoyl chloride (3.0 g, 24 mmol), 2-aminobenzenethiol (4.44 g, 24 mmol) and TMSCl (6.52 g, 60 mmol) in DMF (45 mL) was heated at about 90° C. overnight under argon. The mixture was poured into ice (300 g), and the whole was sonicated for about 20 min and yellow precipitate formed. After filtration, the solid were collected and dissolved in dichloromethane, then washed with aqueous NaHCO3 (150 mL), water (150 mL) and brine (100 mL). The organic phase was dried over Na2SO4, loaded on silica gel, and purified by flash chromatography (hexanes/ethyl acetate 20:1). The fraction one was collected and concentrated and white solid (16) was obtained (2.89 g, 42% yield).

Workup

  1. customthe whole was sonicated for about 20 min
  2. customyellow precipitate formed
  3. filtrationAfter filtration
  4. customthe solid were collected
  5. dissolutiondissolved in dichloromethane
  6. washwashed with aqueous NaHCO3 (150 mL), water (150 mL) and brine (100 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. custompurified by flash chromatography (hexanes/ethyl acetate 20:1)
  9. customThe fraction one was collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ff1193812e8145b4b2cadb1764590f27
Source dataset
uspto-grants-2013_11
Patent number
US08586205B2

Reaction notes

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