2-Bromo-4'-methylacetophenone → HCID 86758662, compound

HRID 2298580Notes

Reaction equation

HRID 2298580 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]([CH3:24])=[CH:20][CH:19]=1)=O>CC(C)=O>[CH3:24][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][CH:20]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758662HCID 86758662, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

103 mg (0.416 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 5 mL of reagent grade acetone. 2-Bromo-4′-methyl acetophenone (0.416 mmol; 89 mg) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and crude product was filtered and washed two times with acetone and purified on a 1 mm silica plate eluting with 20% ethyl acetate/hexane to afford 104 mg (69% yield) of methyl 4-[4-(4-methylphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureto cool
  3. filtrationcrude product was filtered
  4. washwashed two times with acetone
  5. custompurified on a 1 mm silica plate
  6. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-de61a30b65ef47248bdd99c7ed1a6d3d
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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