Sodium → 4-Ethyl-5-methoxy-thiazol-2-ylamine

HRID 1009037Notes

Reaction equation

HRID 1009037 reaction equation
[CH3:1][O-:2].[Na+].[Na].Br[C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH2:12][CH3:13]>CO>[CH2:12]([C:7]1[N:8]=[C:9]([NH2:11])[S:10][C:6]=1[O:2][CH3:1])[CH3:13]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 665201935-Bromo-4-ethylthiazol-2-amine

Product 1

HCID 866309534-Ethyl-5-methoxy-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxide was freshly prepared by dissolving 0.186 g (8.1 mmol) of sodium metal in 12 mL of abs. MeOH. After cooling to 0° C., 5-bromo-4-ethyl-thiazol-2-ylamine (0.519 g, 2.51 mmol) was added and the cooling bath removed. After 45 min, TLC indicated the absence of starting material. The reaction mixture was poured onto crashed ice, twofold extracted with ethyl acetate, washed with brine, dried over sodium sulfate, and evaporated to dryness. Thereby, 0.298 g of the title compound was obtained as brown, rather unstable oil, sufficiently pure to be used for the next step; it should be stored at −28° C.

Workup

  1. customthe cooling bath removed
  2. additionThe reaction mixture was poured
  3. extractiontwofold extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0676b8d7e9e84256a98815705d66bc59
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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