2-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one → Methyl 4-[4-(3,4-ethylenedioxyphenyl)thiazol-2-yl]-5-methylthiothiophene-2-carboxylate

HRID 1597097Notes

Reaction equation

HRID 1597097 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].[O:14]1[C:19]2[CH:20]=[CH:21][C:22]([C:24](=O)[CH2:25]Br)=[CH:23][C:18]=2[O:17][CH2:16][CH2:15]1>CC(C)=O>[CH2:16]1[CH2:15][O:14][C:19]2[CH:20]=[CH:21][C:22]([C:24]3[N:1]=[C:2]([C:3]4[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[S:10])[S:6][C:7]=4[CH3:8])[S:13][CH:25]=3)=[CH:23][C:18]=2[O:17]1

Participants

4

Reactant 2

HCID 27761712-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-oneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86757420Methyl 4-[4-(3,4-ethylenedioxyphenyl)thiazol-2-yl]-5-methylthiothiophene-2-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-(4-(2H,3H-benzo[3,4-e]4-dioxin-6-yl)(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate: 40 mg (0.162 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 2 mL of reagent grade acetone. 1-(2H,3H-benzo[e]1,4-dioxin-6-yl)-2-bromoethan-1-one (0.162 mmol; 42 mg; Maybridge Chemical Co. LTD., Cornwall, U.K.) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and allowed to stir for 2 days after which the reaction solution was concentrated in vacuo. The crude product was dissolved in 50 mL of CH2Cl2 and partitioned between 50 mL of 1 N NaOH (aq.). The organic layer was obtained and dried over sodium sulfate and concentrated to afford 60 mg (90% yield) of methyl 4-[4-(3,4-ethylenedioxyphenyl)thiazol-2-yl]-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureto cool
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe crude product was dissolved in 50 mL of CH2Cl2
  5. custompartitioned between 50 mL of 1 N NaOH (aq.)
  6. customThe organic layer was obtained
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1d6fff9e8ad34c39873c6315e280081a
Source dataset
uspto-grants-2001_09
Patent number
US06291514B1

Reaction notes

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