Magnesium Carbonate → 2-(4-Bromo-2-methyl-phenyl)-thiazole-5-carbaldehyde

HRID 41671

Reaction equation

HRID 41671 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[C:4]([CH3:11])[CH:3]=1.Cl[CH:13]([CH:16]=O)[CH:14]=[O:15].C(=O)([O-])[O-].[Mg+2]>C(COC)OC>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][C:13]([CH:14]=[O:15])=[CH:16][N:8]=2)=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 11029Magnesium CarbonateHCID 147646ChloromalonaldehydeHCID 450407164-Bromo-2-methylthiobenzamide

Product 1

HCID 595846212-(4-Bromo-2-methyl-phenyl)-thiazole-5-carbaldehydeYield 99.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4-bromo-2-methyl-thiobenzamide (3.11 g, 13.5 mmol) and 2-chloromalonaldehyde (2.16 g, 20.3 mmol) in dimethoxyethane (20 ml) is added magnesium carbonate (567 mg, 6.75 mmol) and the resulting mixture stirred at 60° C. under N2 for 3 hours. The crude reaction is then filtered through a plug of silica, washed with EtOAc and the filtrate concentrated to give 2-(4-bromo-2-methyl-phenyl)-thiazole-5-carbaldehyde (3.8 g).

Workup

  1. customThe crude reaction
  2. filtrationis then filtered through a plug of silica
  3. washwashed with EtOAc
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-c12f0fcd0e9043199c989275ad5541f9
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Linked notes

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