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

HRID 1009049Notes

Reaction equation

HRID 1009049 reaction equation
[CH3:1][O-:2].[Na+].[Na].Br[C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12]>CO>[CH3:1][O:2][C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxide was freshly prepared by dissolving 0.408 g (17.7 mmol) of sodium metal in 25 mL of abs. MeOH. After cooling to 0° C., 5-bromo-4-methyl-thiazol-2-ylamine (1.00 g, 5.18 mmol) was added and the cooling bath removed. After 15 Min., TLC indicated the absence of starting material. The reaction mixture was poured onto crashed ice/NH4Cl, twofold extracted with ethyl acetate, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/ethyl acetate=1/1), yielded 0.441 g of the title compound as brown oil; 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 water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-3c3ad3175a7f43a687cc2e1d67a87728
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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