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

HRID 1974824Notes

Reaction equation

HRID 1974824 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-cd6dddbf2f964be1818c8f45f03b94a9
Source dataset
uspto-grants-1994_02
Patent number
US05284821

Reaction notes

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