2-Bromo-1-(3-bromophenyl)ethan-1-one → HCID 86758659, compound

HRID 2298577Notes

Reaction equation

HRID 2298577 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]=[C:20]([Br:24])[CH:19]=1)=O>CC(C)=O>[Br:24][C:20]1[CH:19]=[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:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-oneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758659HCID 86758659, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

99 mg (0.400 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 25 mL of reagent grade acetone. 2-bromo-3′-Bromo acetophenone (0.4 mmol; 111 mg) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and a solid was filtered and dissolved in 5 mL of hot tetrahydrofuran (THF), (Aldrich Chemical Co.) and purified on a 1 mm silica prep plate eluting with 20% ethyl acetate/hexane and dried in vacuo to afford 66 mg (40% yield) of methyl 4-[4-(3-bromophenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureto cool
  3. filtrationa solid was filtered
  4. dissolutiondissolved in 5 mL of hot tetrahydrofuran (THF)
  5. custom(Aldrich Chemical Co.) and purified on a 1 mm silica prep plate
  6. washeluting with 20% ethyl acetate/hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a2b0d71c74c74ff28403007f7c7cb70e
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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