Sodium Methoxide → 5-Methoxy-4-methyl-thiazol-2-ylamine

HRID 1009019Notes

Reaction equation

HRID 1009019 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[CH3:8].[CH3:9][O-:10].[Na+].ClCCl.O>CO>[CH3:9][O:10][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[CH3:8]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amineHCID 21908982Water methylene chloride

Product 1

HCID 204034755-Methoxy-4-methyl-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-4-methyl-thiazol-2-ylamine (0.5 g, 2.59 mmol) was dissolved in methanol abs. (10 mL). The solution was cooled with an ice-bath, then under stirring was added portionwise sodium methoxide (140 mg, 2.59 mmol) The black reaction mixture was stirred for 30 min. at rt then poured into a mixture of dichloromethane/water. The aqueous layer was extracted with two portions of dichloromethane. The combined, organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to obtain the crude product which was used without further purification. MS (EI): m/e 144.1.

Workup

  1. temperatureThe solution was cooled with an ice-bath
  2. customThe black reaction mixture
  3. stirringwas stirred for 30 min. at rt
  4. extractionThe aqueous layer was extracted with two portions of dichloromethane
  5. dry with materialorganic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2984f642682b4c79923f9d53be92f497
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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