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

HRID 412956Notes

Reaction equation

HRID 412956 reaction equation
CC1SC(C([O-])=S)=CC=1.[NH2:10][C:11](=[S:22])[C:12]1[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=1[CH3:17].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=O>CC(C)=O>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:25]2[N:10]=[C:11]([C:12]3[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=3[CH3:17])[S:22][CH:24]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylateHCID 1784259235-Methylthiothiophene-2-carboxylate

Product 1

HCID 86758179Methyl 4-[4-(4-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylateYield 104.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-]4-(4-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate: 30 mg (0.122 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 1.2 mL of reagent grade acetone. 2-bromo-4′-methoxy acetophenone (0.146 mmol; 28 mg; Aldrich Chemical Co.) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and a solid was filtered and washed with methanol and dried in vacuo to afford 46 mg (90% yield) of methyl 4-[4-(4-methoxyphenyl)(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. washwashed with methanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ca6f37ce8d1c42a9897026497f5cc565
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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