Sodium Methoxide → 2-Methoxythiazole-4-carboxylic acid-tert.-butylamide

HRID 5330Notes

Reaction equation

HRID 5330 reaction equation
[CH3:1][O-:2].[Na+].[C:4]([NH:8][C:9]([C:11]1[N:12]=[C:13](Br)[S:14][CH:15]=1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>CO>[C:4]([NH:8][C:9]([C:11]1[N:12]=[C:13]([O:2][CH3:1])[S:14][CH:15]=1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 156638042-Bromo-4-t-butylaminocarbonylthiazole

Product 1

HCID 156724312-Methoxythiazole-4-carboxylic acid-tert.-butylamideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At 25° C., 8.90 g of a 30% strength solution (49 mmol) of sodium methanolate in methanol was added to a solution of 12.00 g (46 mmol) of 2-bromothiazole-4-carboxylic acid-tert.-butylamide in 150 ml of methanol. The mixture was boiled under reflux for four hours, the clear solution was evaporated down, the residue was taken up in 300 ml of diethyl ether and filtered, and the solvent was removed under reduced pressure. There was obtained 9.60 g (98%) of the product as a yellow oil.

Workup

  1. temperatureunder reflux for four hours
  2. customthe clear solution was evaporated down
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c86211829d6b4c1584a76548e6ee953b
Source dataset
uspto-grants-1993_09
Patent number
US05244867

Reaction notes

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