Water → HCID 12831789, compound

HRID 2059058Notes

Reaction equation

HRID 2059058 reaction equation
[CH3:1][C:2]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]([O:15]CC)=[O:14])=[O:12])[S:8][CH:9]=1)([CH3:4])[CH3:3].O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:4][C:2]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]([OH:15])=[O:14])=[O:12])[S:8][CH:9]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 3452736HCID 3452736, compound

Product 1

HCID 12831789HCID 12831789, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 4-(2-methyl-2-propyl)thiazol-2-ylcarbamoylcarboxylate (1.3 g., 5 mmoles) was combined with 40 ml. of water, 20 ml. of ethanol and 5 ml. of 1 N potassium carbonate and the mixture heated on a steam bath for 10 minutes. Completion of reaction was determined by tlc. The solution was stripped of ethanol and the aqueous residue clarified by filtration. The filtrate was cooled in an ice-water bath and the product (1.02 g.) precipitated by acidification with 1 N hydrochloric acid. Recrystallization from ethyl acetate provided purified 4-(2-methyl-2-propyl)thiazol-2-ylcarbamoylcarboxylic acid [0.72 g.; m.p. 198°-200° C. dec.)].

Workup

  1. customCompletion of reaction
  2. filtrationthe aqueous residue clarified by filtration
  3. temperatureThe filtrate was cooled in an ice-water bath
  4. customthe product (1.02 g.) precipitated by acidification with 1 N hydrochloric acid
  5. customRecrystallization from ethyl acetate
  6. customprovided
  7. custompurified 4-(2-methyl-2-propyl)thiazol-2-ylcarbamoylcarboxylic acid [0.72 g

Sources & evidence

ORD record
ord-1688137fcf304273bc174f65c446148b
Source dataset
uspto-grants-1982_03
Patent number
US04321372

Reaction notes

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