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

HRID 1656895Notes

Reaction equation

HRID 1656895 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 (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 to 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-067ea405ac5d4dc8ab3360c1ad59c754
Source dataset
uspto-grants-1993_10
Patent number
US05256633

Reaction notes

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