Thioacetamide → 2-Chloro-5-(2-methyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1988390Notes

Reaction equation

HRID 1988390 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10](=O)[CH2:11]Br)[CH:7]=[CH:6][C:5]=1[Cl:14].[C:16]([NH2:19])(=[S:18])[CH3:17]>C(O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10]2[N:19]=[C:16]([CH3:17])[S:18][CH:11]=2)[CH:7]=[CH:6][C:5]=1[Cl:14]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 588181855-(2-Bromo-acetyl)-2-chloro-benzoic acid methyl ester

Product 1

HCID 588181942-Chloro-5-(2-methyl-thiazol-4-yl)-benzoic acid methyl esterYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(2-bromo-acetyl)-2-chloro-benzoic acid methyl ester (25 mg, 0.09 mmol) and thioacetamide (6.5 mg, 0.08 mmol) in ethanol (2 mL) and stirred at 50° C. for 15 minutes. The mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water, and brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (10 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d8bc77bbe0e40ecadc94596b44d9cec
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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