Water → HCID 12831790, compound

HRID 2059059Notes

Reaction equation

HRID 2059059 reaction equation
[CH:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13]([C:15]([O:17]CC)=[O:16])=[O:14])[S:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13]([C:15]([OH:17])=[O:16])=[O:14])[S:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 12831780Ethyl 4-cyclohexylthiazol-2-ylcarbamoylcarboxylate

Product 1

HCID 12831790HCID 12831790, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 4-cyclohexylthiazol-2-ylcarbamoylcarboxylate (1.41 g., 5 mmole) was combined with 40 ml. of water and 5 ml. of 1 N potassium carbonate (1 equivalent, 2.5 mmole) was heated on a steam bath for 15 minutes. After 10 minutes, tlc (chloroform-1% ethanol) indicated hydrolysis was almost complete. The hot reaction mixture was clarified by filtration, cooled in an ice-water bath and acidified with 10.5 ml. of 1 N hydrochloric acid. Product (1.02 g.) was recovered by filtration. Recrystallization from isopropyl alcohol gave purified 4-cyclohexylthiazol-2-ylcarbamoylcarboxylic acid [625 mg.; m.p. 198.5°-200.5° C. (dec)].

Workup

  1. customhydrolysis
  2. filtrationThe hot reaction mixture was clarified by filtration
  3. temperaturecooled in an ice-water bath
  4. filtrationProduct (1.02 g.) was recovered by filtration
  5. customRecrystallization from isopropyl alcohol
  6. customgave
  7. custompurified 4-cyclohexylthiazol-2-ylcarbamoylcarboxylic acid [625 mg.; m.p. 198.5°-200.5° C. (dec)]

Sources & evidence

ORD record
ord-92ffb636019f4206bf7efeb212defd3a
Source dataset
uspto-grants-1982_03
Patent number
US04321372

Reaction notes

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