Methylamine → Ethyl 2-(methylaminomethyl)thiazole-4-carboxylate

HRID 901946Notes

Reaction equation

HRID 901946 reaction equation
Br[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.[CH3:13][NH2:14]>C1COCC1.CCOC(C)=O>[CH3:13][NH:14][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 45117596Ethyl 2-(methylaminomethyl)thiazole-4-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of ethyl 2-bromomethylthiazole-4-carboxylate (4.25 g, 17 mmol) in THF (50 ml) was added to a solution of methylamine in THF (2M, 30 ml, 60 mmol) drop-wise while cooling to −10° C. The mixture was allowed to warm to room temperature and stirred for a further 30 min. The mixture was diluted with EtOAc and washed with 0.3N potassium hydrogen sulphate solution and brine. The organic phase was dried and reduced to yield ethyl 2-(methylaminomethyl)thiazole-4-carboxylate (3.06 g, 70%) as an orange oil which was used without further purification.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with 0.3N potassium hydrogen sulphate solution and brine
  3. customThe organic phase was dried

Sources & evidence

ORD record
ord-1ea649e3947946aeb03abfdfcdf904d0
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

Loading…