Ethanol → HCID 12831786, compound

HRID 2059055Notes

Reaction equation

HRID 2059055 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C:11]([O:13]CC)=[O:12])=[O:10])=[N:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].O.C(O)C>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C:11]([OH:13])=[O:12])=[O:10])=[N:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 12831777HCID 12831777, compound

Product 1

HCID 12831786HCID 12831786, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 5-ethylthiazol-2-ylcarbamoylcarboxylate (685 mg., 3 mmoles), 1 N potassium carbonate (3 ml., 3 equivalents), water (22 ml.) and ethanol (2--3 ml.) were heated on a steam bath. After 10 minutes, dissolution was nearly complete. After an additional 15 minutes, tlc (chloroform-5% acetic acid) indicated reaction was complete. The cooled reaction mixture was filtered, and crude product (380 mg.) precipitated from the filtrate by acidification with acetic acid. Recrystallization of the crude from isopropyl alcohol gave purified 5-ethylthiazol-2-ylcarbamoylcarboxylic acid [280 mg., m.p. 206.5° C. (dec)].

Workup

  1. dissolutiondissolution
  2. waitAfter an additional 15 minutes
  3. customreaction
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. customcrude product (380 mg.) precipitated from the filtrate by acidification with acetic acid
  7. customRecrystallization of the crude from isopropyl alcohol
  8. customgave
  9. custompurified 5-ethylthiazol-2-ylcarbamoylcarboxylic acid [280 mg., m.p. 206.5° C. (dec)]

Sources & evidence

ORD record
ord-f786ba1668694835b4d0f5018644936c
Source dataset
uspto-grants-1982_03
Patent number
US04321372

Reaction notes

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