Hydrogen Peroxide → 5-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carboxylic acid amide

HRID 1443112Notes

Reaction equation

HRID 1443112 reaction equation
C([O-])([O-])=[O:2].[Na+].[Na+].OO.O.[CH3:10][O:11][CH:12]([O:22][CH3:23])[CH2:13][C:14]1[S:18][C:17]([CH3:19])=[N:16][C:15]=1[C:20]#[N:21]>CC(C)=O>[CH3:23][O:22][CH:12]([O:11][CH3:10])[CH2:13][C:14]1[S:18][C:17]([CH3:19])=[N:16][C:15]=1[C:20]([NH2:21])=[O:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 10340Sodium CarbonateHCID 685419275-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carbonitrile

Product 1

HCID 685435945-(2,2-Dimethoxy-ethyl)-2-methyl-thiazole-4-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2M Na2CO3-solution (64 ml, 127 mmol), H2O2 (30%, 43.3 ml, 424 mmol) and 45 ml water were placed and a solution of 5-(2,2-dimethoxy-ethyl)-2-methyl-thiazole-4-carbonitrile (4.5 g, 21 mmol) in 45 ml acetone was added dropwise at room temperature. The white suspension was stirred for 2 hrs. Acetone was evaporated and the aqueous residue was extracted three times with ethyl acetate. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product (4.8 g, 98%) was used without any further purification for the next step.

Workup

  1. customAcetone was evaporated
  2. extractionthe aqueous residue was extracted three times with ethyl acetate
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (4.8 g, 98%) was used without any further purification for the next step

Sources & evidence

ORD record
ord-86e64a99907f46148763899f6102a118
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

Loading…