Acetone → HCID 86758661, compound

HRID 2298579Notes

Reaction equation

HRID 2298579 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[CH:15](C)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.[CH3:25]C(C)=O>>[CH3:25][C:20]1[CH:21]=[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]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 164522-BromopropiophenoneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758661HCID 86758661, compoundYield 76%

Procedure

48 mg (0.194 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-1-phenylpropan-1-one (0.223 mmol; 48 mg) was added and the solution was allowed to reflux for 5 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 53 mg (76% yield) of methyl 4-(5-methyl-4-phenyl(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 5 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-65e6bcfc31d34cf68f198377ce95c559
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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