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

HRID 456892
Notes
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Reaction equation

HRID 456892 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-50aae2f001974f20a83a8275df6ff95e
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186742B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes