Potassium Carbonate → 2-[(5-Methyl-2-thiazolyl)amino]-2-oxoacetic acid

HRID 2059053Notes

Reaction equation

HRID 2059053 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([C:10]([O:12]CC)=[O:11])=[O:9])=[N:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([C:10]([OH:12])=[O:11])=[O:9])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12831775Ethyl 2-[(5-methyl-2-thiazolyl)amino]-2-oxoacetate

Product 1

HCID 128317832-[(5-Methyl-2-thiazolyl)amino]-2-oxoacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 5-methylthiazol-2-ylcarbamoylcarboxylate (3 g., 14 mmole) was combined with 120 ml. of water and 14 ml. of 1N potassium carbonate and heated on a steam bath for 10 minutes. The mixture was clarified by filtration, cooled in an ice-water bath, acidified with acetic acid, filtered to yield a first crop of product (400 mg.) and evaporated to yield a second crop of product (1.45 g.). The two crops were recrystallized from acetic acid affording purified 5-methylthiazol-2-ylcarbamoylcarboxylic acid [1.12 g., m.p. 212°-213° C. (dec.)].

Workup

  1. filtrationThe mixture was clarified by filtration
  2. temperaturecooled in an ice-water bath
  3. filtrationfiltered
  4. customto yield a first crop of product (400 mg.)
  5. customevaporated
  6. customto yield a second crop of product (1.45 g.)
  7. customThe two crops were recrystallized from acetic acid affording
  8. custompurified 5-methylthiazol-2-ylcarbamoylcarboxylic acid [1.12 g., m.p. 212°-213° C. (dec.)]

Sources & evidence

ORD record
ord-eb2647a5ba98497dbe66fd32546e5db9
Source dataset
uspto-grants-1982_03
Patent number
US04321372

Reaction notes

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