Bromomethyl 2-methoxyphenyl ketone → Methyl 4-[4-(2-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate

HRID 2298581Notes

Reaction equation

HRID 2298581 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][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])=O>CC(C)=O>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1[N:1]=[C:2]([C:3]2[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=2[CH3:8])[S:13][CH:15]=1

Participants

4

Reactant 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86757421Methyl 4-[4-(2-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylateYield 104.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

105 mg (0.424 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-2′-methoxy acetophenone (0.467 mmol; 110 mg) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and the solution concentrated. The crude product was dissolved in 100 mL of CH2Cl2 and washed one time with 50 mL of 1N NaOH. The organic layer was obtained, dried over sodium sulfate, concentrated and purified on a 1 mm silica plate eluting with 20% ethyl acetate/hexane to afford 160 mg (95% yield) of methyl 4-[4-(2-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureto cool
  3. concentrationthe solution concentrated
  4. dissolutionThe crude product was dissolved in 100 mL of CH2Cl2
  5. washwashed one time with 50 mL of 1N NaOH
  6. customThe organic layer was obtained
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified on a 1 mm silica plate
  10. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c7cafe6314084d94b9e1e94edf31ae98
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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