2-Bromo-1-(4-chloro-3-methylphenyl)ethanone → Methyl 4-[4-(4-chloro-3-methylphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate

HRID 2298578Notes

Reaction equation

HRID 2298578 reaction equation
[NH2:1][C:2](=[S:13])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=1[CH3:8].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH3:25])[CH:19]=1)=O>CC(C)=O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=3[CH3:8])[S:13][CH:15]=2)=[CH:19][C:20]=1[CH3:25]

Participants

4

Reactant 2

HCID 5928022-Bromo-1-(4-chloro-3-methylphenyl)ethanoneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758660Methyl 4-[4-(4-chloro-3-methylphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylateYield 70.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

155 mg (0.627 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 10 mL of reagent grade acetone. 2-Bromo-1-(4-chloro-3-methylphenyl)ethan-1-one (0.658 mmol; 163 mg) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and the reaction mixture was concentrated and dissolved in 50 mL of CH2Cl2. The organic layer was washed with 50 mL of 1N HCl (aq.), dried over sodium sulfate and concentrated. The crude product was purified on a 1 mm silica plate eluting with 20% ethyl acetate/hexane to afford 168 mg (68% yield) of methyl 4-[4-(4-chloro-3-methylphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureto cool
  3. concentrationthe reaction mixture was concentrated
  4. dissolutiondissolved in 50 mL of CH2Cl2
  5. washThe organic layer was washed with 50 mL of 1N HCl (aq.)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified on a 1 mm silica plate
  9. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4f9287d3df6f46e1bfc1a26213688d95
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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