Bromomethyl 3-methoxyphenyl ketone → HCID 86583812, compound

HRID 1597096Notes

Reaction equation

HRID 1597096 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].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:22](=O)[CH2:23]Br)[CH:19]=[CH:20][CH:21]=1>CC(C)=O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:22]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:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583812HCID 86583812, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-[4-(3-methoxyphenyl)(1,3-thiazol-2-yl)-5-methylthiothiophene-2-carboxylate: 32 mg (0.133 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. 3′-Methoxy-2-bromo acetophenone (0.155 mmol; 36 mg; Aldrich Chemical Co.) was added and the solution was allowed to reflux for 2.5 h. The solution was allowed to cool and a solid was filtered and washed with methanol and dried in vacuo. The solid was purified on 1 mm silica plate eluting with 25% ethyl acetate/hexane to afford 31 mg (63% yield) of methyl 4-[4-(3-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate.

Workup

  1. temperatureto reflux for 2.5 h
  2. temperatureto cool
  3. filtrationa solid was filtered
  4. washwashed with methanol
  5. customdried in vacuo
  6. customThe solid was purified on 1 mm silica plate
  7. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-70722cd983354e4c9a577eb69ee991c1
Source dataset
uspto-grants-2001_09
Patent number
US06291514B1

Reaction notes

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